Ethanol → 2-Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, ethyl ester

HRID 1579256Notes

Reaction equation

HRID 1579256 reaction equation
C(O)C.[CH3:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.Cl[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1(C)C=CC=CC=1>[CH3:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]2[O:11][CH:15]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7751Ethyl chloroacetateHCID 312444-Methoxybenzaldehyde

Product 1

HCID 860252-Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
24 °C

Procedure

Ethanol free sodium ethoxide was mixed with 200 ml. of toluene and cooled to 0°C. A solution of p-methoxybenzaldehyde, 56.0 g. (0.412 mole), and ethyl chloroacetate, 50.5 g. (0.412 mole), in 200 ml. of toluene was added at such a rate that the temperature remained below 10°C. After stirring at 24°C. for 16 hours, the mixture was washed twice with 400 ml. portions of water and dried over anhydrous sodium sulfate. The solvent was evaporated to give a yellow liquid of about 80% purity (81.2 g.). The liquid solidified on standing at 5°C. and was further purified by washing with a small volume of cold ethanol to give pale yellow crystals of ethyl 3-(4-methoxyphenyl)-2,3-epoxypropionate having a melting point of between 40° and 43°C.

Workup

  1. customremained below 10°C
  2. washthe mixture was washed twice with 400 ml
  3. dry with materialportions of water and dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customto give a yellow liquid of about 80% purity (81.2 g.)
  6. customon standing at 5°C.
  7. customwas further purified
  8. washby washing with a small volume of cold ethanol

Sources & evidence

ORD record
ord-e81dafce0b1543b3bcf4fe3a979f4386
Source dataset
uspto-grants-1976_01
Patent number
US03931188

Reaction notes

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