Epichlorohydrin → 1-[5-Methyl-2-(oxiranylmethoxy)phenyl]ethanone

HRID 2051688Notes

Reaction equation

HRID 2051688 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].Cl[CH2:13][CH:14]1[CH2:16][O:15]1.C[O-].[Na+]>CO>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:13][CH:14]2[CH2:16][O:15]2)=[C:3]([C:9](=[O:11])[CH3:10])[CH:4]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 150682-Hydroxy-5-methylacetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 203795011-[5-Methyl-2-(oxiranylmethoxy)phenyl]ethanoneYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 20 parts of 1-(2-hydroxy-5-methylphenyl)ethanone, 50.5 parts of (chloromethyl)oxirane and 40 parts of methanol are added dropwise 25 parts of sodium methoxide solution 30%. Upon completion, stirring is continued for 1 hour at room temperature. The reaction mixture is filtered and the filtrate is evaporated. The residue is dissolved in methylbenzene. The latter is washed with water, dried, filtered and evaporated. The residue is distilled, yielding 15 parts (55%) of 1-[5-methyl-2-(oxiranylmethoxy)phenyl]ethanone; bp. 140°-150° C. at 0.3 mm. pressure.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated
  3. dissolutionThe residue is dissolved in methylbenzene
  4. washThe latter is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe residue is distilled

Sources & evidence

ORD record
ord-6a676bef4fe94a7c92b0a24a8ba51055
Source dataset
uspto-grants-1980_01
Patent number
US04181802

Reaction notes

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