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ChemicalBook CAS DataBase List (S)-(+)-Glycidyl butyrate
65031-96-1

(S)-(+)-Glycidyl butyrate synthesis

4synthesis methods
-

Yield: 99.4 % ee

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 20; for 1 h;

Steps:

2
To 1.2 L of a methylene chloride solution of (R)-3-chloro-l,2-propanediol (200g, 99.5% ee) was added 519 g of potassium phosphate tribasic, and then the obtained solution was refluxed, under stirring, for 3 hours. The resulting solution was cooled to 0°C, and 220 g of triethylamine and 212 g of butyryl chloride were drop wisely added to the solution. After additional stirring for 1 hour at a room temperature, the reaction mixture was successively washed with 2.2 L of 5% aqueous potassium carbonate solution, 2 L of IN aqueous hydrogen chloride solution, and 1 L of water. The organic layer was dried with 50 g of anhydrous sodium sulfate and filtrated. The methylene chloride was evaporated under reduced pressure. Fractional distillation (90°C/19 mmHg) of the resulting residue gave 243 g of the targeted compound:-Yield: 93.1%- Chemical purity: 99.4%- Optical purity (GC) 99.4% ee

References:

RSTECH CORPORATION WO2006/19202, 2006, A1 Location in patent:Page/Page column 7

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