Water → Methyl 3,3-di(4-ethylphenyl)-2,3-epoxypropionate

HRID 433929Notes

Reaction equation

HRID 433929 reaction equation
Cl[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH2:7]([C:9]1[CH:24]=[CH:23][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=2)=[O:14])=[CH:11][CH:10]=1)[CH3:8].C([O-])C.[Na+].O>C1COCC1>[CH2:21]([C:18]1[CH:19]=[CH:20][C:15]([C:13]2([C:12]3[CH:11]=[CH:10][C:9]([CH2:7][CH3:8])=[CH:24][CH:23]=3)[O:14][CH:2]2[C:3]([O:5][CH3:6])=[O:4])=[CH:16][CH:17]=1)[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7295Methyl chloroacetateHCID 2723922Sodium ethoxideHCID 122283294,4'-Diethylbenzophenone

Product 1

HCID 18756192Methyl 3,3-di(4-ethylphenyl)-2,3-epoxypropionateYield 59.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 15 ml (168 mmol) of methyl chloroacetate and 20 g (84 mmol) of 4,4′-diethylbenzophenone in 20 ml of THF was added dropwise to a suspension of 9.1 g (168 mmol) of sodium ethanolate in 80 ml of THF at −10° C. The mixture was warmed to room temperature and stirred for 2 hours. The mixture was added to water and extracted with ether. The organic phase was washed with sodium bicarbonate solution and citric acid solution and dried over magnesium sulfate, and the solvent was distilled off. 15.4 g of a crude oil were isolated and were immediately employed further.

Workup

  1. extractionextracted with ether
  2. washThe organic phase was washed with sodium bicarbonate solution and citric acid solution
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-bc4c158dff2a4b75ab428a6890c5114a
Source dataset
uspto-grants-2003_12
Patent number
US06670367B1

Reaction notes

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