Dimethyl Sulfate → Oxirane, 2-methyl-2-[4-(2-methylpropyl)phenyl]-

HRID 652309

반응식

HRID 652309 반응식
[C:1]1(SC)C=CC=CC=1.S(OC)(OC)(=O)=O.COS([O-])(=O)=O.C1([S+](C)C)C=CC=CC=1.[CH2:31]([C:35]1[CH:40]=[CH:39][C:38]([C:41](=[O:43])[CH3:42])=[CH:37][CH:36]=1)[CH:32]([CH3:34])[CH3:33].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:31]([C:35]1[CH:36]=[CH:37][C:38]([C:41]2([CH3:1])[O:43][CH2:42]2)=[CH:39][CH:40]=1)[CH:32]([CH3:34])[CH3:33]

참가 물질

7

반응물 5

HCID 6497Dimethyl SulfateHCID 7520ThioanisoleHCID 14798Sodium HydroxideHCID 932144'-IsobutylacetophenoneHCID 21201015Phenyldimethylsulfonium methylsulfate

생성물 1

HCID 10330171Oxirane, 2-methyl-2-[4-(2-methylpropyl)phenyl]-수율 86.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

24.8 g (0.2 mole) of thioanisole was heated to 90° C. with stirring, 27.8 g (0.22 mole) of dimethyl sulfate was added thereto at 90°-95° C. over a period of 30 minutes and stirred for another 30 minutes at the same temperature. To the reaction mixture, 100 ml of toluene was added portionwise so as to maintain the temperature above 80° C. and then the mixture was cooled gradually with stirring to afford a suspension of phenyldimethylsulfonium methylsulfate in quantititative yield. To the suspension, 26.4 g (0.15 mole) of p-isobutylacetophenone and 16.0 g (0.4 mole) of powdered sodium hydroxide was added and the mixture was stirred for 8 hours at 50° C. The reaction mixture was worked up in the same manner as described in Example 6 to afford 24.7 g of 2-(4-isobutylphenyl)-1,2-epoxypropane in 86.7% yield.

후처리

  1. stirringstirred for another 30 minutes at the same temperature
  2. temperatureto maintain the temperature above 80° C.
  3. temperaturethe mixture was cooled gradually
  4. stirringwith stirring
  5. customto afford
  6. stirringthe mixture was stirred for 8 hours at 50° C

출처 및 근거

ORD 기록
ord-15177263dc044f7d8c798298986e14c2
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04670607

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