Water → 3-Isopropyl-5-methylphenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester

Participants

Reaction Steps

A mixture of 3-isopropyl-5-methylphenoxyacetic acid (prepared above, 6.0 g, 28.8 mmol), 2-(p-toluenesulfonyl)ethanol (5.77 g, 28.8 mmol), and p-toluenesulfonic acid hydrate (p-TsOH.H2O) (0.5 g) in 100 mL of toluene was refluxed with Dean-Stark trap for 3 h. Then water was added and the mixture was extracted with CH2Cl2. The combined organic layers were washed with saturated NaHCO3 solution (2×), dried over MgSO4, and concentrated to give 3-isopropyl-5-methylphenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 64, 11.0 g, 98%) as a light brown oil.

Provenance & Evidence