Oxalyl chloride → Ethyl 4-tert-butyl-2-methylbenzoate

Participants

Reaction Steps

To a 100 mL round bottom flask was charged with acid 101a (630 mg, 3.3 mmol) in CH2Cl2 (20 mL) was added oxalyl chloride (4.9 mL, 9.8 mmol, 2.0M solution in CH2Cl2) followed by DMF (1 drop). After the reaction was stirred at room temperature for 8 h, it was concentrated. To the residue was added Et2O (25 mL) and the mixture was concentrated. This repeated to removed any excess oxalyl chloride. The residue was dissolved in CH2Cl2 (15 mL) and EtOH (15 mL). After the reaction was stirred at room temperature for 30 min, it was concentrated. The residue was dissolved in EtOAc (15 mL) and this organic phase was washed with aqueous HCl (15 mL, 1M), H2O (15 mL), brine (15 mL), dried with Na2SO4 and concentrated. The crude 101b (660 mg, 91%) was used without further purification.

Provenance & Evidence