Dichloromethane → Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Participants

Reaction Steps

8.7 g (50 mmol) of dimethyl adipate, anhydrous aluminum trichloride (20 g) and 100 ml of dry dichloromethane were cooled to 0° C. under an ice bath. At 0° C., triethylamine (dried with sodium hydroxide, 45 ml) was added dropwise and slowly. After addition, the ice bath was removed and the reaction was carried out at room temperature for 4 hours, being monitored with TLC. After the reaction was completed, the reaction liquid was poured into an ice-water mixture slowly, which was stirred for 30 min. The organic layer was separated and the aqueous layer was extracted with dichloromethane (50 ml×2). The organic layers were combined and washed with water and then with saturated NaCl, dried with anhydrous magnesium sulfate, and filtrated. The solvent was distilled off under reduced pressure to give 5.1 g of 2-oxocyclopentanecarboxylate methyl ester. The yield was 71.8%.

Provenance & Evidence