Hexane → 8-Hydroxy-9-(4-pentoxyphenoxy)-5-nonynoic acid

Participants

Reaction Steps

A dry flask equipped with an addition funnel and a mechanical stirrer under Ar was charged with 100 ml of HMPA and 9.7 g of 5-hexynoic acid. The flask was cooled in an ice water bath and a solution of n-BuLi in hexane (118 ml, 0.189 mole) was added dropwise. The resulting reaction mixture was stirred for 1.5 hr and then a solution of 24.5 g of 2-(4-pentoxyphenoxymethyl)oxirane, the product of Example 14a, in 20 ml of HMPA was added and stirring was continued for 2 days. The reaction mixture was poured into water and extracted with Et2O three times. The ether solution was washed with aqueous NH4OH twice. The aqueous solution was acidified with HCl and extracted with Et2O. The ether solution was washed with saturated NaCl solution, dried over MgSO4. Solvent was removed to give the crude product which was recrystallized in cyclohexane to give the title compound, mp 58.0°-60.0°.

Provenance & Evidence