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

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%.

1. additionAfter addition
2. customthe ice bath was removed
3. customthe reaction liquid
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with dichloromethane (50 ml×2)
6. washwashed with water
7. dry with materialwith saturated NaCl, dried with anhydrous magnesium sulfate
8. filtrationfiltrated
9. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-6ab274bec417465e94565143ec799d46

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018213B2