Methanol → HCID 178520922, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of trans-4-(4-chlorophenyl)cyclohexanecarbaldehyde (compound of formula (IVa) (approximately 9.33 g, 41.9 mmol, assuming quantitative conversion for preparation from trans-4-(4-chlorophenyl)cyclohexanecarboxylic acid) in EtOAc (100 mL) was charged with MeOH (40 mL), water (10 mL) and sodium metabisulfite (4.38 g, 0.55 eq). The resulting slurry was heated to 51° C., and stirred at this temperature for 45 min, the slurry was cooled to 20° C. over 1 hr then held for 30 min. The slurry was filtered and the cake washed with EtOAc (2×20 mL). The product was de-liquored then dried further in a 45° C. oven under reduced pressure to yield the title compound as a colourless solid (11.04 g, 81%). 1H NMR (400 MHz, d6-DMSO) δH 1.10-1.43 (4H, m, CH-alkyl), 1.70-1.80 (3H, m, CH-alkyl), 1.87-1.94 (1H, m, CH-alkyl), 2.12-2.21 (1H, m, CH-alkyl) 2.37-2.47 (1H, m, OH), 3.67 (1H, m, H-6), 4.79 (1H, m, H-9), 7.20-7.34 (4H, m, H-1 and H-2).

Provenance & Evidence