Dimethyl Sulfide → 2-(4-Chlorophenyl)-2-[1-(4-chlorophenyl)-2-methylpropan-2-yl]oxirane

HRID 1380919Notes

Reaction equation

HRID 1380919 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.CSC.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=O)([CH3:21])[CH3:20])=[CH:14][CH:13]=1.C[O-].[Na+]>C(#N)C>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2([C:19]([CH3:21])([CH3:20])[CH2:22][C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)[CH2:7][O:6]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6497Dimethyl SulfateHCID 10942334Sodium MethoxideHCID 132174061,3-Bis(4-chlorophenyl)-2,2-dimethylpropan-1-one

Product 1

HCID 132174072-(4-Chlorophenyl)-2-[1-(4-chlorophenyl)-2-methylpropan-2-yl]oxiraneYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 59.2 g (0.47 mol) of dimethyl sulphate and 32 g (0.517 mol) of dimethyl sulphide in 270 ml of acetonitrile is stirred at room temperature for 5 days. A solution of 81.5 g (0.2655 mol) of 4-chlorophenyl 4-chlorophenyl-tert.-butyl ketone in 80 ml of acetonitrile is then added dropwise at 20° to 25° C. in the course of about 2 hours. 28.7 g (0.53 mol) of sodium methylate are added at the same temperature. The entire reaction mixture is subsequently stirred for 12 hours and is then concentrated in vacuo. The residue is stirred overnight with a mixture of 200 ml of ethyl acetate and 150 ml of water. The organic phase is separated off, dried over sodium sulphate and concentrated in vacuo. 72.6 g (85.2% of theory) of crude 2-(4-chlorophenyl)-2-(4-chlorophenyl-tert.-butyl)-oxirane are obtained and are further reacted directly. ##STR156##

Workup

  1. customThe entire reaction mixture
  2. concentrationis then concentrated in vacuo
  3. stirringThe residue is stirred overnight with a mixture of 200 ml of ethyl acetate and 150 ml of water
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54c3ad8514594c9e9aec5cbead11cc9c
Source dataset
uspto-grants-1986_04
Patent number
US04584308

Reaction notes

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