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

HRID 1380922Notes

Reaction equation

HRID 1380922 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 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 87 g of 4-chlorophenyl 2-(p-chlorophenoxy)-prop-2-yl 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 introduced at the same temperature, and the mixture is subsequently stirred for 12 hours and then concentrated. 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. 49 g (76% of theory) of crude 2-(4-chlorophenyl)-2-[2-(p-chlorophenoxy)-prop-2-yl]-oxirane are obtained, and are further reacted directly. ##STR159##

Workup

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

Sources & evidence

ORD record
ord-9ec0dec5e4c94ff7bbfbcc7d38190acf
Source dataset
uspto-grants-1986_04
Patent number
US04584308

Reaction notes

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