Dimethyl Sulfide → 2-[2-(4-Chlorophenoxy)propan-2-yl]-2-(4-chlorophenyl)oxirane

HRID 979453Notes

Reaction equation

HRID 979453 reaction equation
S(OC)(O[CH3:5])(=O)=O.CSC.[Cl:11][C:12]1[CH:30]=[CH:29][C:15]([O:16][C:17]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[O:21])([CH3:19])[CH3:18])=[CH:14][CH:13]=1.C[O-].[Na+]>C(#N)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]2([C:17]([O:16][C:15]3[CH:14]=[CH:13][C:12]([Cl:11])=[CH:30][CH:29]=3)([CH3:19])[CH3:18])[CH2:5][O:21]2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6497Dimethyl SulfateHCID 10942334Sodium MethoxideHCID 198424902-(4-Chlorophenoxy)-1-(4-chlorophenyl)-2-methylpropan-1-one

Product 1

HCID 198424852-[2-(4-Chlorophenoxy)propan-2-yl]-2-(4-chlorophenyl)oxiraneYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 59.2 g (0.47 mole) of dimethyl sulphate and 32 g (0.517 mole) of dimethyl sulphide in 270 ml of acetonitrile is allowed to stir at room temperature for 5 days. Then, at 20° to 25° C., a solution of 87 g of 4-chlorophenyl 2-(p-chlorophenoxy)-2-propyl ketone in 80 ml of acetonitrile is added dropwise within about 2 hours. At the same temperature, 28.7 g (0.53 mole) of sodium methylate are added, the mixture is allowed to stir for 12 hours and then evaporated. The residue is vigorously stirred with a mixture of 200 ml of ethyl acetate and 150 ml of water overnight. The organic phase is separated off, dried over sodium sulphate and evaporated in vacuo. 49 g (76% of theory) of crude 2-(4-chlorophenyl)-2-[2-(p-chlorophenoxy)-2-propyl]oxirane are obtained, and this is immediately reacted further. ##STR47##

Workup

  1. stirringto stir for 12 hours
  2. customevaporated
  3. stirringThe residue is vigorously stirred with a mixture of 200 ml of ethyl acetate and 150 ml of water overnight
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-9e7c1c43da3c49f98130f50da40e1719
Source dataset
uspto-grants-1987_05
Patent number
US04668660

Reaction notes

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