Methyl iodide → HCID 10867613, compound

To a solution of lithium diisopropylamide (LDA) in THF (1 liter), which had been prepared from diisopropylamine (52 g) and a 1.6 M solution of n-butyl lithium in hexane (319 ml), was added dropwise a solution of ethyl 4-chlorophenylacetate (97.3 g) in THF (100 ml) at a temperature of -45° to -40° C. under an atmosphere of nitrogen gas. At the same temperature, the reaction mixture was stirred for 0.5 hours, and methyl iodide (73 g) was added dropwise thereto, followed by allowing the temperature to gradually increase to room temperature. The reaction mixture was poured into ice-water and extracted with ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure to give ethyl 2-(4-chlorophenyl)propionate (yield, 89.4 g), b.p., 108°-114° C. at 1.0 mmHg.

1. extractionextracted with ether
2. washThe organic layer was washed with water
3. dry with materialdried over anhydrous magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. distillationThe resulting residue was distilled under reduced pressure

ORD record

ord-774c4c29d0114830aa37a688eebc74c4

Source dataset

uspto-grants-1995_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05451607