Characterization Data

Mild and Efficient Method for the Reduction of Carboxylic Acid to Alcohol using Ortho -NosylOXY

4.6. Characterization Data

(9H-Fluoren-9-yl)methyl (2-hydroxyethyl)carbamate 2a.

White solid (125 mg, 89%), mp 141-143 °C; ¹H NMR (600 MHz, CDCl3) δ 7.76-7.75 (d, J = 7.2 Hz, 2H), 7.59-7.57 (d, J

= 7.2 Hz, 2H), 7.41-7.38 (t, J = 7.2 Hz, 2H), 7.32-7.29 (t, J = 7.2 Hz, 2H), 4.42-4.41 (d, J = 6.6 Hz, 2H), 4.21-4.19 (t, J = 6.6 Hz, 1H), 3.70-3.68 (t, J = 4.8 Hz, 2H), 3.34-3.32 (m, 2H); ¹³C NMR (150 MHz, CDCl3) δ 157.3, 144.0, 141.4, 127.8, 127.2, 125.1, 120.1, 66.8, 62.2, 47.3, 43.5; FT-IR (KBr) 3328, 2859, 1675, 1541, 1277, 1071, 739 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C17H18NO3

284.1287, found 284.1264.

(9H-Fluoren-9-yl)methyl (1-hydroxypropan-2-yl)carbamate 2b.

White solid (126 mg, 85%), mp 153-155 °C; ¹H NMR (600 MHz, CDCl3) δ 7.77-7.76 (d, J = 7.2 Hz, 2H), 7.60-7.58 (d, J

= 7.8 Hz, 2H), 7.41-7.39 (t, J = 7.2 Hz, 2H), 7.33-7.30 (t, J = 6.6 Hz, 2H), 4.42-4.41 (d, J = 6.6 Hz, 2H), 4.22-4.20 (t, J = 6.6 Hz, 1H), 3.83 (br s, 1H), 3.67 (br s, 1H), 3.53 (br s, 1H), 1.18-1.17 (d, J = 6.6 Hz, 3H); ¹³C NMR (150 MHz, CDCl3) δ 156.7, 144.08, 141.5, 127.8, 127.2, 125.1, 120.1, 66.9, 66.8, 49.1, 47.4, 17.4; FT-IR (KBr) 3324, 2926, 1686, 1545, 1268, 1043, 736 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C18H20NO3 298.1443, found 298.1437.

(9H-Fluoren-9-yl)methyl (1-hydroxypropan-2-yl)carbamate 2c.

Semi-solid (112 mg, 72%), ¹H NMR (600 MHz, CDCl3) δ 7.77- 7.76 (d, J = 7.8 Hz, 2H), 7.59-7.58 (d, J = 7.8 Hz, 2H), 7.42-7.39 (t, J = 7.8 Hz, 2H), 7.33-7.31 (t, J = 7.8 Hz, 2H), 4.86 (br s, 1H), 4.40 (br s, 2H), 4.20-4.18 (t, J = 6.6 Hz, 1H), 3.59 (s, 2H), 1.26 (s, 6H); ¹³C NMR (150 ) δ 156.3, 144.0, 141.5, 127.9, 127.2, 125.1, 120.2, 70.3, 66.4, 54.7, 47.5, 24.7;

Chapter 4 Reduction of Carboxylic Acids to Alcohols

FT-IR (KBr) 3419, 2969, 2928, 1703, 1535, 1091, 740 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C19H22NO3 312.1600, found 312.1592.

(9H-Fluoren-9-yl)methyl (1-hydroxypropan-2-yl)carbamate 2d.

White solid (132 mg, 81%), mp 130-132 °C, ¹H NMR (600 MHz, CDCl3) δ 7.77-7.76 (d, J = 7.2 Hz, 2H), 7.60-7.59 (d, J

= 7.2 Hz, 2H), 7.41-7.39 (t, J = 7.2 Hz, 2H), 7.33-7.30 (t, J = 7.2 Hz, 2H), 4.88 (br s, 1H), 4.48-41 (m, 2H), 4.23-4.21 (t, J

= 6.6 Hz, 1H), 3.71-3.62 (m, 2H), 3.47 (br s, 1H), 1.87-1.83 (m, 1H), 0.96-0.92 (m, 6H);

13C NMR (150 MHz, CDCl3) δ 157.3, 144.0, 141.5, 127.8, 127.2, 125.1, 120.1, 66.7, 63.8, 58.7, 47.5, 29.3, 19.6, 18.7; FT-IR (KBr) 3443, 2923, 2848, 1637, 1020, 738 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C20H24NO3 326.1756, found 326.1762.

(S)-(9H-Fluoren-9-yl)methyl (1-hydroxy-4-methylpentan-2-yl)carbamate 2e.

White solid (142 mg, 84%), mp 126-128 °C; ¹H NMR (600 MHz, CDCl3) δ 7.77-7.76 (d, J = 7.2 Hz, 2H), 7.59-7.58 (d, J

= 7.2 Hz, 2H), 7.41-7.39 (t, J = 7.2 Hz, 2H), 7.33-7.30 (t, J = 7.2 Hz, 2H), 4.77-4.76 (d, J = 7.8 Hz, 1H), 4.45-4.44 (d, J = 6.6 Hz, 2H), 4.22-4.20 (t, J = 6.6 Hz, 1H), 3.77 (br s, 1H), 3.67-3.66 (m, 1H), 3.53-3.50 (m, 1H), 1.63 (br, s,1H), 1.37-1.31 (m, 2H), 0.93-0.92 (d, J = 4.8 Hz, 6H); ¹³C NMR (150 MHz, CDCl3) δ 156.9, 144.0, 141.5, 127.8, 127.2, 125.2, 120.1, 66.7, 66.1, 51.5, 47.5, 40.5, 24.9, 23.2, 22.3; FT-IR (KBr) 3393, 2952, 1687, 1576, 1267, 739 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C21H26NO3 340.1913, found 340.1926.

(S)-(9H-Fluoren-9-yl)methyl (1-hydroxy-4-methylpentan-2-yl)carbamate 2f.

White solid (147 mg, 79%), mp 163-165 °C; ¹H NMR (600 MHz, CDCl3) δ 7.76-7.75 (d, J = 7.8 Hz, 2H), 7.55-7.52 (t, J = 7.8 Hz, 2H), 7.41-7.38 (t, J = 7.2 Hz, 2H), 7.31-7.20 (m, 7H), 4.96 (br s, 1H), 4.41-4.37 (m, 2H), 4.19-4.17 (t, J = 6.6 Hz, 1H), 3.92 (br s, 1H), 3.67-3.58 (m, 2H), 2.85 (br s, 2H); ¹³C NMR (150 MHz, CDCl3) δ 156.6, 144.0, 141.4, 137.7, 129.4, 128.7, 127.8, 127.2, 126.7, 125.1, 120.1, 66.7, 64.0, 54.2, 47.3, 37.4; FT-IR (KBr) 3443, 2924, 2852, 1632, 1024, 740 cm^-1; HRMS (ESI) m/z: [M+H]⁺

Chapter 4 Reduction of Carboxylic Acids to Alcohols

(S)-(9H-Fluoren-9-yl)methyl (1-hydroxy-4-methylpentan-2-yl)carbamate 2h.

White solid (144 mg, 80%), mp 129-131 °C; ¹H NMR (600 MHz, CDCl3) δ 7.76-7.26 (m, 13H), 5.51 (br s, 1H), 4.84 (br s, 1H), 4.44-4.43 (d, J = 5.4 Hz, 2H), 4.21 (br s, 1H), 3.88 (br s, 2H); ¹³C NMR (150 MHz, CDCl3) δ 156.6, 144.0, 141.5, 139.2, 129.0, 128.0, 127.8, 127.2, 126.7, 125.2, 120.1, 66.9, 66.5, 57.2, 47.4; FT-IR (KBr) 3344, 2923, 2853, 1687, 1540, 1018, 736 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C23H22NO3 360.1600, found 360.1608.

(S)-(9H-Fluoren-9-yl)methyl (1-hydroxy-4-methylpentan-2-yl)carbamate 2i.

White solid (142 mg, 83%), mp 120-122 °C; ¹H NMR (600 MHz, CDCl3) δ 7.77-7.76 (d, J = 7.8 Hz, 2H), 7.60-7.58 (d, J = 7.8 Hz, 2H), 7.41-7.39 (t, J = 7.8 Hz, 2H), 7.33-7.30 (t, J = 7.2 Hz, 2H), 4.91 (br s, 1H), 4.47-4.43 (m, 2H), 4.23-4.20 (t, J = 6.6 Hz, 1H), 3.73-3.62 (m, 2H), 3.54 (br s, 1H), 1.51-1.47 (m, 2H), 1.15-1.10 (m, 1H), 0.92-0.90 (t, J = 6.6 Hz, 6H); ¹³C NMR (150 MHz, CDCl3) δ 157.2, 144.1, 141.5, 127.8, 127.2, 125.1, 120.1, 66.7, 63.7, 57.6, 47.5, 36.1, 25.6, 15.7, 11.5; FT-IR (KBr) 3480, 2924, 2854, 1671, 1541, 1045, 736 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C21H26NO3

340.1913, found 340.1903.

(R)-(9H-Fluoren-9-yl)methyl (1-(tert-butoxy)-3-hydroxypropan-2-yl)carbamate 2j.

White solid (140 mg, 76%), mp 95-97 °C; ¹H NMR (600 MHz, CDCl3) δ 7.77-7.76 (d, J = 7.8 Hz, 2H), 7.61-7.60 (d, J = 7.2 Hz, 2H), 7.41-7.39 (t, J = 6.6 Hz, 2H), 7.33-7.30 (t, J = 7.2 Hz, 2H), 5.57 (br s, 1H), 4.40-4.39 (d, J = 7.2 Hz, 2H), 4.24-4.22 (t, J = 6.6 Hz, 1H), 3.89-3.87 (m, 1H), 3.81-3.80 (m, 1H), 3.74-3.71 (m, 1H), 3.618-3.613 (d, J = 3 Hz, 2H), 1.20 (s, 9H); ¹³C NMR (150 MHz, CDCl3) δ 156.5, 143.9, 141.3, 127.7, 127.1, 125.1, 120.0, 66.8, 64.1, 63.1, 51.9, 47.2, 27.4; FT-IR (KBr) 3339, 2926, 1668, 1540, 1089, 739 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C22H28NO4

370.2018, found 370.2033.

Chapter 4 Reduction of Carboxylic Acids to Alcohols

(R)-(9H-Fluoren-9-yl)methyl (1-(tert-butoxy)-3-hydroxypropan-2-yl)carbamate 2k.

Semi solid (137 mg, 72%); ¹H NMR (600 MHz, CDCl3) δ 7.77- 7.76 (d, J = 7.2 Hz, 2H), 7.61-7.60 (d, J = 7.2 Hz, 2H), 7.41- 7.39 (t, J = 7.2 Hz, 2H), 7.33-7.30 (t, J = 7.2 Hz, 2H), 5.29 (br s, 1H), 4.43-4.39 (m, 2H), 4.24-4.22 (t, J = 7.2 Hz, 1H), 3.96- 3.94 (m, 1H), 3.72-3.61 (m, 3H), 1.21 (s, 9H), 1.17-1.16 (d, J = 6.6 Hz, 2H); ¹³C NMR (150 MHz, CDCl3) δ 157.2, 144.1, 141.5, 127.8, 127.2, 125.2, 120.1, 67.4, 67.0, 63.9, 57.3, 47.4, 28.8, 20.3; FT-IR (KBr) 3438, 2976, 2925, 1727, 1518, 1068, 738 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C23H30NO4 384.2175, found 384.2190.

(R)-(9H-Fluoren-9-yl)methyl (1-(tert-butoxy)-3-hydroxypropan-2-yl)carbamate 2l.

White solid (139 mg, 78%), mp 137-139 °C; ¹H NMR (600 MHz, CDCl3) δ 7.77-7.76 (d, J = 7.8 Hz, 2H), 7.60-7.58 (d, J = 7.8 Hz, 2H), 7.41-7.39 (t, J = 7.8 Hz, 2H), 7.33-7.31 (t, J = 7.8 Hz, 2H), 5.01 (br s, 1H), 4.45-4.44 (d, J = 4.2 Hz, 2H), 4.22-4.20 (t, J = 6.6 Hz, 1H), 3.80-3.79 (m, 1H), 3.70-3.62 (m, 2H), 2.54-2.51 (m, 2H), 2.10(s, 3H), 1.87-1.76 (m, 2H); ¹³C NMR (150 MHz, CDCl3) δ 156.8, 144.0, 141.5, 127.9, 127.2, 125.1, 120.1, 66.7, 65.0, 53.6, 52.5, 47.4, 30.8, 15.7; FT-IR (KBr) 3321, 2921, 2838, 1690, 1542, 1284,1037 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C20H24NO3S 358.1477, found 358.1469.

(R)-(9H-Fluoren-9-yl)methyl (1-(tert-butoxy)-3-hydroxypropan-2-yl)carbamate 2m.

White solid (111 mg, 69%), mp 79-81 °C; ¹H NMR (600 MHz, CDCl3) δ 7.77-7.76 (d, J = 7.2 Hz, 2H), 7.60-7.59 (d, J = 7.2 Hz, 2H), 7.42-7.39 (t, J = 7.2 Hz, 2H), 7.33-7.30 (t, J = 7.2 Hz, 2H), 4.46-4.38 (m, 2H), 4.26-4.23 (t, J = 7.2 Hz, 1H), 4.00-3.99 (m, 1H), 3.69-3.59 (m, 2H), 3.54-3.50 (m, 1H), 3.40-3.36 (m, 1H), 2.06-2.01 (m, 1H), 1.91-1.87 (m, 1H), 1.84- 1.80 (m, 1H), 1.63-1.59 (m, 1H); ¹³C NMR (150 MHz, CDCl3) δ 157.3, 144.1, 141.5, 127.9, 127.2, 125.1, 120.1, 67.7, 67.1, 60.9, 53.6, 47.5, 28.7, 24.2; FT-IR (KBr) 3442, 2925, 1677, 1422, 1107, 739 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C20H22NO3 324.1600, found 324.1628.

Chapter 4 Reduction of Carboxylic Acids to Alcohols

(R)-(9H-Fluoren-9-yl)methyl (1-(tert-butoxy)-3-hydroxypropan-2-yl)carbamate 2o.

White solid (144 mg, 65%), mp 111-113 °C; ¹H NMR (600 MHz, CDCl3) δ 7.76-7.75 (d, J = 7.8 Hz, 2H), 7.56-7.55 (d, J = 7.8 Hz, 2H), 7.41-7.38 (t, J = 7.8 Hz, 2H), 7.32-7.29 (t, J = 7.8 Hz, 2H), 7.06-7.07 (d, J = 7.8 Hz, 2H), 6.91-6.90 (d, J = 7.8 Hz, 2H), 5.01 (br s, 1H), 4.25-4.36 (m, 2H), 4.19-4.17 (t, J = 7.2 Hz, 1H), 3.89 (br s, 1H), 3.67-3.55 (m, 2H), 2.81-2.80 (d, J = 6.6 Hz, 2H), 1.31 (s, 9H); ¹³C NMR (150 MHz, CDCl3) δ 156.6, 154.1, 144.0, 141.4, 132.5, 129.8, 127.8, 127.2, 125.1, 124.4, 120.1, 78.5, 66.7, 63.9, 54.2, 47.4, 36.7, 28.9; FT-IR (KBr) 3332, 2974, 2927, 1689, 1539, 1023, 737 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C28H31NO4 446.2331, found 446.2353.

(R)-(9H-Fluoren-9-yl)methyl (1-(tert-butoxy)-3-hydroxypropan-2-yl)carbamate 2p.

White solid (199 mg, 63%), mp 82-84 °C; ¹H NMR (600 MHz, CDCl3) δ 7.73-7.72 (d, J = 7.2 Hz, 2H), 7.56-7.55 (d, J = 7.2 Hz, 2H), 7.36-7.34 (t, J = 7.2 Hz, 2H), 7.26-7.24 (m, 2H), 6.18 (br s, 2H), 5.57 (br s, 1H), 4.36-4.35 (d, J = 7.2 Hz, 2H), 4.14-4.10 (m, 2H), 3.64-3.55 (m, 3H), 3.21 (br s, 2H), 2.89 (br s, 1H), 2.56 (s, 1H), 2.49 (s, 1H), 2.06 (s, 1H), 1.57-1.52 (br s, 4H), 1.42 (s, 6H);

13C NMR (150 MHz, CDCl3) δ 159.0, 157.2, 156.5, 143.9, 141.4, 138.5, 132.7, 132.4, 127.8, 127.2, 125.3, 124.9, 120.1, 117.8, 86.6, 66.9, 64.8, 47.3, 43.3, 29.9, 28.7, 25.7, 22.9, 19.5, 18.1, 14.3,12.6; FT-IR (KBr) 3444, 2924, 2854, 1708, 1548, 1451, 1255, 1101, 738 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C34H42N3O4S 635.2903, found 635.2921.

(S)-(9H-Fluoren-9-yl)methyl tert-butyl (6-hydroxyhexane-1,5-diyl)dicarbamate 2q.

White solid (154 mg, 68%), mp 139-141 °C; ¹H NMR (600 MHz, CDCl3) δ 7.76-7.75 (d, J = 7.8 Hz, 2H), 7.60-7.58 (d, J = 7.8 Hz, 2H), 7.41-7.38 (t, J = 7.8 Hz, 2H), 7.32-7.30 (t, J = 7.8 Hz, 2H), 5.09 (br s, 1H), 4.41 (br s, 1H),4.42-4.41 (d, J = 4.2 Hz, 2H), 4.22-4.19 (t, J = 6.6 Hz, 1H), 3.64-3.60 (m, 3H), 3.17-3.06 (m, 2H), 1.72-1.47 (m, 4H), 1.42 (s, 9H), 1.38-1.33 (m, 2H); ¹³C NMR (150 MHz, CDCl ) δ 156.9, 156.5, 144.0, 141.4, 127.8, 127.2, 125.2, 120.1, 79.4,

Chapter 4 Reduction of Carboxylic Acids to Alcohols

66.7, 64.8, 53.0, 47.4, 39.8, 30.6, 30.0, 28.5, 22.8; FT-IR (KBr) 3362, 2927, 2855, 1687, 1533, 1036, 737 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C26H35N2O5 455.2546, found 455.2560.

(R)-(9H-Fluoren-9-yl)methyl (1-(tert-butoxy)-3-hydroxypropan-2-yl)carbamate 2r.

White solid (180 mg, 62%), mp 110-112 °C; ¹H NMR (600 MHz, CDCl3) δ 7.76-7.74 (t, J = 7.2 Hz, 2H), 7.58-7.56 (d, J = 7.8 Hz, 2H), 7.42-7.20 (m, 19H), 4.84 (br s, 1H), 4.39-4.38 (d, J = 6.6 Hz, 1H), 4.20-4.18 (t, J = 6 Hz, 1H), 3.52-3.48 (m, 3H), 2.50-2.42 (m, 2H); ¹³C NMR (150 MHz, CDCl3) δ 173.1, 156.0, 143.7, 141.9, 141.4, 128.6, 127.9, 127.7, 127.2, 126.8, 125.1, 120.1, 74.3, 67.3, 50.4, 47.1, 36.3, 29.8; FT-IR (KBr) 3445, 2854, 1642, 1031, 739, 698 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C38H35N2O4

583.2597, found 583.2605.

(S)-tert-Butyl (1-hydroxy-3-phenylpropan-2-yl)carbamate 2s.

White solid (106 mg, 78%), mp 91-93 °C; ¹H NMR (600 MHz, CDCl3) δ 7.33-7.23 (m, 5H), 4.80-4.79 (d, J = 5.4 Hz, 1H), 3.89 (br, s, 1H), 3.69 (br, s, 1H) , 3.58 (br, s, 1H), 2.86-2.85 (d, J = 6.0 Hz, 2H), 1.43 (s, 9H); ¹³C NMR (150 MHz, CDCl3) δ 156.3, 137.9, 129.4, 128.7, 126.7, 79.9, 64.5, 53.9, 37.6, 28.5; FT-IR (KBr) 3356, 2925, 1687, 1528, 1170, 1006 cm^-1; HRMS (ESI) m/z: [M+Na]⁺ calcd for C14H22NO3Na 274.1419, found 274.1421.

(S)-tert-Butyl (1-hydroxy-3-phenylpropan-2-yl)carbamate 2t.

White solid (90 mg, 76%), mp 128-130 °C; ¹H NMR (600 MHz, CDCl3) δ 7.36-7.26 (m, 5H), 5.32 (br, s, 1H), 4.77 (br, s, 1H) , 3.82 (br, s, 2H), 1.43 (s, 9H); ¹³C NMR (150 MHz, CDCl3) δ 156.3, 139.6, 128.9, 127.9, 126.7, 80.1, 67.0, 57.0, 28.5; FT-IR (KBr) 3247, 2976, 1672, 1552, 1054, 702 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C13H19NO3Na 260.1263, found 260.1273.

Chapter 4 Reduction of Carboxylic Acids to Alcohols

(S)-Benzyl (1-hydroxypropan-2-yl)carbamate 2u.

White solid (114 mg, 80%), mp 86-88 °C; ¹H NMR (600 MHz, CDCl3) δ 7.37-7.15 (m, 10H), 5.07 (s, 2H), 5.01 (br s, 1H), 3.96 (br s, 1H), 3.70-3.58 (m, 2H) , 2.87-2.86 (d, J = 6.6 Hz, 2H); ¹³C NMR (150 MHz, CDCl3) δ 156.7, 137.7, 136.4, 129.4, 128.7, 128.6, 128.2, 128.1, 66.9, 63.8, 54.2, 37.4; FT-IR (KBr) 3479, 2927, 2869, 1691, 1538, 1256, 1015, cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C17H20NO3 286.1443, found 286.1462.

(S)-Benzyl (1-hydroxypropan-2-yl)carbamate 2v.

White solid (86 mg, 83%), mp 79-81 °C; ¹H NMR (600 MHz, CDCl3) δ 7.34 (s, 5H), 5.08 (s, 2H), 3.82 (br, s, 1H), 3.64 (br, s, 1H) , 3.51 (br, s, 1H), 1.15-1.14 (d, J = 6.8 Hz, 3H); ¹³C NMR (150 MHz, CDCl3) δ 156.7, 136.5, 128.6, 128.29, 128.25, 66.9, 66.6, 49.0, 17.3; FT-IR (KBr) 3310, 2971, 1687, 1539, 1076, 693 cm^-1; HRMS (ESI) m/z: [M+H]⁺ calcd for C11H16NO3

210.1130, found 210.1126.

Phenylmethanol 4a.

Liquid (88 mg, 81%); ¹H NMR (600 MHz, CDCl3) δ 7.36-7.29 (m, 5H), 4.67 (s, 2H); ¹³C NMR (150 MHz, CDCl3) δ 140.8, 128.3, 127.3, 126.9, 64.6; FT-IR (KBr) 3443, 2927, 1613, 1247, 1031, 736 cm^-1. (4-Methoxyphenyl)methanol 4b.

White solid (127 mg, 84%), mp 72-74 °C; ¹H NMR (600 MHz, CDCl3) δ 7.28-7.27 (d, J = 7.2 Hz, 2H), 6.89-6.88 (d, J = 7.8 Hz, 2H), 4.59 (s, 2H), 3.80 (s, 3H); ¹³C NMR (150 MHz, CDCl3) δ 158.9, 133.2, 128.6, 113.8, 64.5, 55.2; FT-IR (KBr) 3432, 2923, 1636, 1021, 737 cm^-1 (4-Bromophenyl)methanol 4c.

White solid (160 mg, 86%), mp 72-74 °C; ¹H NMR (600 MHz, CDCl3) δ 7.48-7.47 (d, J = 8.4 Hz, 2H), 7.23-7.22 (d, J = 8.4 Hz, 2H), 4.64 (s, 2H); ¹³C NMR (150 MHz, CDCl3) δ 139.9, 131.7,

Chapter 4 Reduction of Carboxylic Acids to Alcohols

128.7, 121.6, 64.7; FT-IR (KBr) 3480, 2923, 2854, 1639, 1009, 504 cm^-1; LRMS (ESI) m/z: [M+H]⁺ calcd for C7H8BrO 186.9759, found 186.2207.

(4-Nitrophenyl)methanol 4d.

Yellow solid (155 mg, 89%), mp 93-95 °C; ¹H NMR (600 MHz, CDCl3) δ 8.22-8.21 (d, J = 8.4 Hz, 2H), 7.54-7.53 (d, J = 8.4 Hz, 2H), 4.84 (s, 2H); ¹³C NMR (150 MHz, CDCl3) δ 148.4, 147.4, 127.1, 123.9, 64.1; FT-IR (KBr) 3476, 2924, 1640, 1515, 1345, 1055, 736 cm^-1; LRMS (ESI) m/z: [M+Na]⁺ calcd for C7H8NO3Na 176.0324, found 176.0097.

4-(Hydroxymethyl)benzonitrile 4e.

Semi-solid (109 mg, 80%); ¹H NMR (600 MHz, CDCl3) δ 8.22- 8.21 (d, J = 8.4 Hz, 2H), 7.54-7.53 (d, J = 8.4 Hz, 2H), 4.84 (s, 2H); ¹³C NMR (150 MHz, CDCl3) δ 146.6, 132.4, 127.1, 119.0, 111.0, 64.1; FT-IR (KBr) 3442, 2923, 2855, 2230, 1047, 816 cm^-1; HRMS (ESI) m/z:

[M+H]⁺ calcd for C8H8NO 134.0606, found 138.0602.

Naphthalen-2-ylmethanol 4f.

White solid (111 mg, 70%), mp 68-70 °C; ¹H NMR (600 MHz, CDCl3) δ 7.84-7.80 (m, 4H), 7.49-7.47 (m, 3H), 4.84 (s, 2H); ¹³C NMR (150 MHz, CDCl3) δ 138.51, 133.57, 133.1, 128.5, 128.0, 127.9, 126.3, 126.1, 125.6, 125.3, 65.6; FT-IR (KBr) 3380, 2923, 2853, 1632, 1041, 818 cm^-1; LRMS (ESI) m/z: [M+H]⁺ calcd for C11H11O 159.0810, found 159.0319.

2-(4-Nitrophenyl)ethanol 4g.

Semi solid (133 mg, 79%); ¹H NMR (600 MHz, CDCl3) δ 8.16-8.14 (d, J = 8.4 Hz, 2H), 7.40-7.39 (d, J = 9.6 Hz, 2H), 3.93-3.90 (t, J = 6.6 Hz, 2H), 2.98-2.96 (t, J = 6.6 Hz, 2H);

13C NMR (150 MHz, CDCl3) δ 146.8, 146.7, 129.8, 123.6, 62.8, 38.8; FT-IR (KBr) 3441, 2923, 2853, 1640, 1517, 1346 cm^-1.

Chapter 4 Reduction of Carboxylic Acids to Alcohols