3-Methoxybenzaldehyde → (9,10-Dihydro-anthracen-9-yl)-(3-methoxy-phenyl)-methanol

Participants

Reaction Steps

Cool a THF (50 mL) solution of 9,10-dihydroanthracene (5.10 g, 28 mmol) to 0° C. and add 1.6M n-BuLi (19 mL, 30 mmol) slowly. After 30 minutes, add m-anisaldehyde (3.4 mL, 28 mmol) to the dark brown solution. Allow the reaction to slowly warm to ambient temperature and then carefully quench with aqueous saturated NH4Cl. Shake the entire reaction with water/EtOAc and dry the organic layer (MgSO4). Concentrate under reduced pressure to give 9.4 g light tan oil. Purify by column chromatography using 25% EtOAc/hexane to give 4.7 g (53%) as a colorless oil that rapidly crystallized, mp 105.9° C. HPLC shows 94% purity.

Provenance & Evidence