Bisphenol A diglycidyl ether diacrylate → 2-(4-Fluorophenyl)-2-methoxy-3,3-dimethyloxirane

HRID 376953Notes

Reaction equation

HRID 376953 reaction equation
Br[C:2]([CH3:13])([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4].FC1C=CC([C:21](=[O:25])C(C)C)=CC=1.CC(C1C=CC(OCC(O)COC(C=C)=O)=CC=1)(C1C=CC(OCC(O)COC(C=C)=O)=CC=1)C.C[O-].[Na+]>CO.ClC1C=CC=CC=1>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2([O:25][CH3:21])[C:2]([CH3:13])([CH3:12])[O:4]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 92212Bisphenol A diglycidyl ether diacrylateHCID 27828291-(4-Fluorophenyl)-2-methylpropan-1-oneHCID 10942334Sodium MethoxideHCID 131131752-Bromo-1-(4-fluorophenyl)-2-methylpropan-1-one

Product 1

HCID 131131762-(4-Fluorophenyl)-2-methoxy-3,3-dimethyloxirane

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 7964ChlorobenzeneSolvent

Procedure

100.32 g (0.41 mol) of 2-bromo-1-(4-fluorophenyl)-2-methylpropan-1-one, prepared by brominating 1-(4-fluorophenyl)-2-methylpropan-1-one (as is described in EP-A-3002), are dissolved in 80 ml of dry methanol and 24.3 g (0.45 mol) of sodium methoxide in a solvent mixture of 60 ml dry methanol and 120 ml of chlorobenzene are added dropwise at 20° C. The methanol is then distilled off and the chlorobenzene solution is concentrated. The liquid crude product (90.8 g) is further purified by distillation at 60° C. and 0.2 mm Hg.

Workup

  1. additionare added dropwise at 20° C
  2. distillationThe methanol is then distilled off
  3. concentrationthe chlorobenzene solution is concentrated
  4. distillationThe liquid crude product (90.8 g) is further purified by distillation at 60° C.

Sources & evidence

ORD record
ord-53e21ef81ad649b19a9efa67caf37ef5
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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