Sulfuric Acid → 4-(4-Chlorophenyl)oxane-4-carboxylic acid

Participants

Reaction Steps

To a solution of (4-chlorophenyl)acetonitrile (1.15 g, 7.59 mmol) in DMF (11.5 mL) at 10° C., was added sodium tert-butoxide (0.80 g, 8.34 mmol). The resulting mixture was aged for 10 minutes and then treated with bis(2-chloroethyl)ether (1.19 g, 8.34 mmol). The mixture was aged at 10° C. for 1 hour, warmed to ambient temperature and treated with a second portion of sodium tert-butoxide (0.80 g, 8.34 mmol). After 10 minutes, the mixture was quenched with a 1.0M H3PO4 solution and extracted with EtOAc (2×25 mL). The combined extracts were washed with saturated brine, dried (MgSO4), and concentrated in vacuo to give a brown solid. The product was dissolved in 1,4-dioxane (5 mL) and treated with a 9.0M H2SO4 solution at 100° C. for 48 hours. The cooled mixture was then brought to pH=10 and extracted with diethyl ether (2×25 mL). The aqueous phase was acidified to pH=2 with 5N HCl, and the resulting precipitate was collected by vacuum filtration. The solid was dried under vacuum at 50° C. overnight. MS m/e=241.2 (M+H)+.

Provenance & Evidence