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

Participants

Reaction Steps

LiAlH4 (5.3 g, 140 mmol) and about 200 ml of THF were blanketed with argon in a reaction vessel and diethyl 2-(4′-hexyloxyphenyl)terephthalate (40 g, 100 mmol) (cf. C1) together with a further 50 ml of THF were slowly added dropwise from a dropping funnel. The reaction mixture was stirred vigorously during this addition. The mixture was subsequently refluxed for about one hour. The reaction mixture was brought to RT and, while cooling in a water bath and blanketing with 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 twice with chloroform. The organic phases were washed once with H2O and subsequently evaporated. The crude product obtained was recrystallized from hexane/ethyl acetate (5:1).

Provenance & Evidence