Hydrochloric Acid → 2,6-Dimethyl-4-(pyrrolidin-1-ylmethyl)phenol

Participants

Reaction Steps

NaB(OAc)3H (22.1 g, 0.104 mol) was added in portions for 15 min to a mixture of pyrrolidine (8.1 mL, 0.098 mol) and 3,5-dimethyl-4-hydroxybenzaldehyde (12.5 g, 0.083 mol) in CH2Cl2 (100 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon Ar. The mixture was stirred for 20 h and cooled with an ice bath. Concentrated HCl (19 mL) was added. The organic layer was separated and discarded. The aqueous one was alkalized with 10 N NaOH to pH 9 (30 mL) and extracted with chloroform (2×100 mL). The combined extracts were dried with Na2SO4, and evaporated to give the title compound (14 g, 82%) was obtained as white crystals. LCMS-data: 206.1 and 207.1 (M+H)+ (calculated for C13H19NO 205.1). 1H NMR (400 MHz)-data (DMSO-d6, J, Hz): 7.99 (br s, 1H, OH); 6.80 (s, 2H, ArH); 3.36 (s, 2H, CH2); 2.32-2.41 (m, 4H, CH2CH2CH2CH2); 2.13 (s, 6H, (CH3)2); 1.61-1.70 (m, 4H, CH2CH2CH2CH2).

Provenance & Evidence