Toluene → 5-(Benzyloxy)pentanoic acid

Participants

Reaction Conditions

Reaction Steps

δ-Valerolactone (50 g) and toluene (500 mL) were mixed. To the mixture were added potassium hydroxide (158 g) and benzyl bromide (178 mL). The mixture was stirred at 125° C. overnight. To the reaction mixture was added water (350 mL) at ice temperature. The organic layer was removed, and the aqueous layer was washed with tert-butyl methyl ether (150 mL×3). To the resulting aqueous layer were added concentrated hydrochloric acid (75 mL) and 6 N hydrochloric acid (40 mL) at ice temperature. The mixture was extracted with ethyl acetate (250 mL, 100 mL). The combined organic layer was washed with brine (100 mL), then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (79.2 g) as a crude product.

Provenance & Evidence