Ethanol → Ethyl 2-(2-chlorophenyl)acetate

Temperature

90 °C

A solution of 2-chlorophenylacetic acid (10.12 g, 59.3 mmol) in EtOH (150 mL, 2576 mmol) in a 500 mL round bottom flask was treated with concentrated H2SO4 (0.700 mL, 8.28 mmol) and heated at 90° C. for 16 hours. The solution was concentrated in vacuo, diluted with 1N NaOH(aq) (200 mL), and extracted with EtOAc (2×200 mL). The combined organic layers were washed with 1N NaOH(aq) (200 mL), water (100 mL), and brine (100 mL). The organic layer was dried over MgSO4, concentrated, and dried in vacuo to give ethyl 2-(2-chlorophenyl)acetate (11.344 g). MS m/e=217 (M+H)+.

1. concentrationThe solution was concentrated in vacuo
2. additiondiluted with 1N NaOH(aq) (200 mL)
3. extractionextracted with EtOAc (2×200 mL)
4. washThe combined organic layers were washed with 1N NaOH(aq) (200 mL), water (100 mL), and brine (100 mL)
5. dry with materialThe organic layer was dried over MgSO4
6. concentrationconcentrated
7. customdried in vacuo

ORD record

ord-07db39e73347461c87daf4475d2e0216

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07635715B2