Hydrochloric Acid → benzyl (2S)-2-hydroxypropanoate

(S)-Lactic acid (60 g) and 75 g of benzyl bromide were dissolved in 500 ml of dimethylformamide, to which 72.5 g of potassium iodide and 150 g of potassium carbonate were added with ice cooling. After the mixture was stirred at room temperature for 6 hours, 500 ml of ethyl acetate and 500 ml of diisopropyl ether were added thereto. The supernatant layer was obtained by decantation and the precipitate was washed with 100 ml of diisopropyl ether. The organic solutions thus obtained were combined and poured into 200 ml of 5N-hydrochloric acid under ice-cooling. The separated organic layer was washed with 250 ml of 2N-hydrochloric acid, 100 ml of an aqueous solution of sodium thiosulfate and 100 ml of an aqueous solution of sodium chloride successively, and dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was distilled under reduced pressure to give 29.3 g of (S)-benzyl lactate (yield: 37%) as a colorless oil.

1. additionwere added with ice cooling
2. customThe supernatant layer was obtained by decantation
3. washthe precipitate was washed with 100 ml of diisopropyl ether
4. customThe organic solutions thus obtained
5. temperaturecooling
6. washThe separated organic layer was washed with 250 ml of 2N-hydrochloric acid, 100 ml of an aqueous solution of sodium thiosulfate and 100 ml of an aqueous solution of sodium chloride successively
7. dry with materialdried over magnesium sulfate
8. distillationAfter the solvent was distilled off under reduced pressure
9. distillationthe residue was distilled under reduced pressure

ORD record

ord-db26f50661924014bd405b2e30806e60

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05677464