3-Isopropoxybenzaldehyde → (3-Isopropoxyphenyl)methanol

Participants

Reaction Steps

To a solution of 3-Isopropoxy-benzaldehyde 14-1 (20 g, 122 mmol) in methanol (400 mL), sodium borohydride (5 g) is added in several portions at 0° C. The resulting mixture is then stirred at rt for 3 h. The reaction is quenched by addition of saturated NH4OH. Extracted (EtOAc), concentrated, a colorless oil 14-2 (MH+, 166) is obtained and use without purification. Re-dissolve (3-Isopropoxy-phenyl)-methanol 14-2 in ether (244 mL) PBr3 (11.5 mL, 122 mmol) is added dropwise at 0° C. The reaction mixture is stirred at 0° C. then rt for 3 h, quenched (MeOH), extracted (EtOAc), concentrated, a colorless oil 14-3 is obtained. (MH+, 288)

Provenance & Evidence