Water → 4-Iodobenzyl alcohol

Participants

Reaction Conditions

Reaction Steps

(Acheson, R. M.; Lee, G. C. M. J. Chem. Soc. Perkin Trans. I 1987, 2321–2332.) To a stirred suspension of sodium borohydride (5.68 g, 150 mmol, 2.0 equiv) in 50 mL dioxane at 0° C. was added dropwise a solution of 4-iodobenzoyl chloride (19.99 g, 75 mmol, 1.0 equiv) in 50 mL dioxane over 25 min. The resulting mixture was heated to 100° C. for 90 min under a reflux condenser then cooled to 0° C. 50 mL H2O was added cautiously under a flowing stream of nitrogen. [CAUTION: Evolves gas!] The mixture was extracted 3×125 mL CH2Cl2 and the combined organic extracts were washed with 2× H2O, 2×0.1N HCl, 2×1N NaOH, H2O, and brine, dried (MgSO4), filtered, and evaporated to yield 16.9 g of crude 4-iodobenzyl alcohol as a white solid, determined by NMR to contain 78% desired product with the remainder residual starting material and 4-iodobenzoic acid. The crude product was used without further purification. mp: 61.0–66.5° C. TLC Rf=0.27 (3:1 hexanes/EtOAc). IR (film): 3306, 1005, 791. 1H-NMR (400 MHz, CDCl3): δ 7.69 (d, 2H, J=8.3, C4-H, C6-H), 7.12 (d, 2H, J=8.5, C3-H, C7-H), 4.66 (br d, 2H, J=4.1, C1—H2), 1.67 (br t, 1H, C1-OH). 13C-NMR (125 MHz, CDCl3): δ 140.4, 137.6, 128.8, 93.0, 64.6. EI-MS m/z (rel int): 234 (M+, 100).

Provenance & Evidence