Methanol → 2,2-Diphenyloxirane

HRID 1683356Notes

Reaction equation

HRID 1683356 reaction equation
S(=O)(=O)(O)O.CSC.CO.[C:11](O)(C)(C)C.[C:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[K+]>>[C:17]1([C:16]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:23][CH2:11]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 6

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 1118Sulfuric AcidHCID 3102BenzophenoneHCID 6386tert-ButanolHCID 14797Potassium Hydroxide

Product 1

HCID 935642,2-Diphenyloxirane

Procedure

Sulphuric acid (23.7 g at 98%, 0.237 moles) was added dropwise, with stirring, to dimethylsulphide (20.0 g at 98%, 0.316 moles) over 60 minutes, maintaining the temperature below 26° C. Methanol (5.0 g, 0.156 mole) was added slowly to the stirred mixture maintaining the temperature below 31° C. The reaction mixture was stirred for 41/2 hours and head overnight unagitated at room temperature. Tertiary butanol (3.6 g, 0.048 mole) and benzophenone (27.4 g, 0.15 mole) were added to the reaction mixture. Potassium hydroxide flake (43.4 g, 0.73 mole) was added in 10 equal aliquots over 3 hours while maintaining the temperature below 40° C. The reaction was monitored by GC and then stirred overnight at room temperature.

Workup

  1. temperaturemaintaining the temperature below 26° C
  2. temperaturemaintaining the temperature below 31° C
  3. waithead overnight unagitated at room temperature
  4. temperaturewhile maintaining the temperature below 40° C
  5. stirringstirred overnight at room temperature

Sources & evidence

ORD record
ord-7377de9cb3384830a45c128508eb003c
Source dataset
uspto-grants-1997_06
Patent number
US05637727

Reaction notes

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