Methanol → [5-(3,5,5,8,8-Pentamethyl-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-3-yl)thiophene-3-yl]carboxylic acid

Participants

Reaction Steps

A mixture of methyl [5-(3,5,5,8,8-pentamethyl-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-3-yl)-thiophene-3-yl]carboxylate (2.1 g, 5.4 mmol), lithium hydroxide (2g, 48 mmol), methanol (1 ml) and water (1 ml) in 30 ml of THF was heated under reflux for 6 h. After concentrating in a rotary evaporator under vacuum at 40° C., adding water, ethyl ether and acidifying with a concentrated hydrochloric acid solution to pH 1, the organic phase was washed twice with water, dried over magnesium sulfate and concentrated in a rotary evaporator under vacuum at 40° C. The solids obtained were washed with heptane.

Provenance & Evidence