Acetophenone → Ethyl methylphenylglycidate

HRID 2291013Notes

Reaction equation

HRID 2291013 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[NH2-].[Na+]>C1C=CC=CC=1>[CH3:16][CH2:15][O:14][C:12]([CH:11]1[O:3][C:1]1([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2])=[O:13]

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 7751Ethyl chloroacetateHCID 24533Sodium amide

Product 1

HCID 6501Ethyl methylphenylglycidateYield 63.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 120 g of acetophenone, 123 g of ethyl chloroacetate, and 200 ml of benzene was added 47.2 g of powder sodium amide over a period of 2 hours at 15° C. At the end of a 2-hour stirring at room temperature, the resulting red colored mixture was poured into 700 g of ice water. The organic phase was extracted with benzene, dried, and stripped of the solvent. The residue was fractionally distilled, yielding 130 g of ethyl 3-methyl-3-phenylglycidate having a boiling point of 107°-113° C./3 mmHg.

Workup

  1. extractionThe organic phase was extracted with benzene
  2. customdried
  3. distillationThe residue was fractionally distilled

Sources & evidence

ORD record
ord-f2512768afe542789c16147f11c3be78
Source dataset
uspto-grants-1986_10
Patent number
US04619888

Reaction notes

Loading…