Toluene → 2-(3-Methoxyphenyl)oxirane

HRID 654240Notes

Reaction equation

HRID 654240 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7].[OH-].[Na+].[CH3:13]OS([O-])(=O)=O.C([S+](C)C)CCCCCCCCCCC.C1(C)C=CC=CC=1>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]1[O:7][CH2:13]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 115693-MethoxybenzaldehydeHCID 14798Sodium HydroxideHCID 3016616Dodecyldimethylsulphonium methyl sulphate

Product 1

HCID 979032-(3-Methoxyphenyl)oxirane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-methoxybenzaldehyde (13.4 g, 0.098 mol), a solution of sodium hydroxide (200 g) in water (200 ml), dodecyl-dimethylsulfonium methyl sulfate (51 g, 0.15 mol) and toluene (150 ml) is stirred for 17 hours. Ice is then added and the organic phase is separated, washed with water (3×50 ml), dried over sodium sulfate, filtered and concentrated under reduced pressure. The above product is recovered from the thus obtained residue by distillation at 135°-140° C. and 30 mmHg.

Workup

  1. additionIce is then added
  2. customthe organic phase is separated
  3. washwashed with water (3×50 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. distillationThe above product is recovered from the thus obtained residue by distillation at 135°-140° C.

Sources & evidence

ORD record
ord-31024d6dc8914547a849fcbbc34f8761
Source dataset
uspto-grants-1992_07
Patent number
US05130339

Reaction notes

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