Dimethyl Sulfide → 2-tert-Butyl-2-[(4-chlorophenoxy)methyl]oxirane

HRID 371485

반응식

HRID 371485 반응식
CSC.S([O:9][CH3:10])(OC)(=O)=O.C[O-].[Na+].[Cl:14][C:15]1[CH:28]=[CH:27][C:18]([O:19][CH2:20][C:21](=O)[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:16]=1>C(#N)C>[Cl:14][C:15]1[CH:28]=[CH:27][C:18]([O:19][CH2:20][C:21]2([C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:10][O:9]2)=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 1068Dimethyl SulfideHCID 6497Dimethyl SulfateHCID 905182-Butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-HCID 10942334Sodium Methoxide

생성물 1

HCID 127636212-tert-Butyl-2-[(4-chlorophenoxy)methyl]oxirane수율 84%

시약·촉매·용매 1

HCID 6342Acetonitrile용매3회

실험 절차

A solution of 162 ml (2.2 moles) of dimethyl sulphide in 400 ml of absolute acetonitrile was added to a solution of 189 ml (2.0 moles) of dimethyl sulphate in 1,200 ml of absolute acetonitrile at room temperature. The reaction mixure was stirred overnight at room temperature. 118.8 g (2.2 moles) of sodium methylate were then added. The mixture was stirred for 30 minutes and a solution of 272 g (1.2 moles) of 1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-one in 600 ml of absolute acetonitrile was then added dropwise in the course of 30 minutes. The reaction mixture was subsequently stirred overnight. It was then concentrated, the residue was partitioned between water and ethyl acetate, the organic phase was separated off, washed twice with water and once with saturated sodium chloride solution, dried over sodium sulphate and concentrated and the residue was distilled in vacuo. 242.4 g (84% of theory) of 2-(4-chlorophenoxy-methyl)-2-tert.-butyl-oxirane of boiling point 115°-22° C./0.003 mm Hg column and of melting point 50°-52° were obtained.

후처리

  1. stirringThe mixture was stirred for 30 minutes
  2. waitThe reaction mixture was subsequently stirred overnight
  3. concentrationIt was then concentrated
  4. customthe residue was partitioned between water and ethyl acetate
  5. customthe organic phase was separated off
  6. washwashed twice with water and once with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. distillationthe residue was distilled in vacuo

출처 및 근거

ORD 기록
ord-4ee8f622e2c445e49182ca7d9bdd8be6
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04532341

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