Dichloromethane → HCID 19767559, compound

Participants

Reaction Steps

To a solution of 2-tert-butyl-8,8-dimethyl-5,6,7,8-tetrahydronaphthol (9.5 g, 40.5 mmole) and 1,1-dichloromethyl methyl ether (5.17 g, 45 mmole) in dry dichloromethane (200 ml) stannic chloride (15.63 g, 60 mmole) was added dropwise at -58°. The mixture was warmed to 0° over 45 minutes, poured into ice water (300 ml) and extracted with diethyl ether (3×150 ml). The ether extracts were washed with water and aqueous saturated sodium chloride, dried and evaporated to give 3-tert-butyl-5,5-dimethyl-4-hydroxy-5,6,7,8-tetrahydro-1-naphthaldehyde as a crystalline solid (9.49 g, 90%), m.p. 143°-45°.

Provenance & Evidence