Sulfuric Acid → 2,5-Bishydroxymethyl-4'-hexyloxybiphenyl

Participants

Reaction Steps

LiAlH4 (5.3 g, 140 mmol) was added to about 200 ml of THF under a blanket of argon and diethyl 2-(4′-hexyloxyphenyl)terephthalate (40 9, 100 mmol) (cf. C1) together with a further 50 ml of THF was slowly added dropwise from a dropping funnel. The reaction mixture was vigorously stirred during this addition. It was subsequently refluxed for about one hour. The reaction mixture was brought to RT and, with water bath cooling and under a blanket of argon, ice water was carefully added dropwise until gas evolution had ceased. Dilute (10% strength) sulfuric acid was subsequently added dropwise until the turbid gray mixture was clear. The phases were separated by addition of chloroform and the aqueous phase was shaken with chloroform (twice). The organic phases were washed once with H2O and subsequently evaporated. The resulting crude product was recrystallized from hexane/ethyl acetate (5/1).

Provenance & Evidence