Monobenzone → p-Benzyloxy-(1-methylheptyloxy)benzene

HRID 579914

반응식

HRID 579914 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C1(C)C=CC(S(O[CH:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])(=O)=O)=CC=1.CCCCCC[C@@H](O)C>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 7638MonobenzoneHCID 14798Sodium HydroxideHCID 2723888(+)-2-OctanolHCID 3912199p-Toluenesulfonic acid 1-methylheptyl ester

생성물 1

HCID 13878908p-Benzyloxy-(1-methylheptyloxy)benzene

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

p-Benzyloxyphenol (50 g), ethanol (150 ml) and 50% NaOH aqueous solution (25 g) were mixed with stirring, followed by pouring in the mixture, optically active 1-methylheptyl p-toluenesulfonate derived from S-(+)-2-octanol, heating the mixture under reflux for 4 hours, distilling off most of ethanol, extracting with toluene, washing with acid, alkali and water, drying, concentrating and purifying the concentrate according to column chromatography with activated alumina (150 g) to obtain oily p-benzyloxy-(1-methylheptyloxy)benzene (68.6 g), which was then subjected to hydrogenolysis with 5% Pd-C catalyst in ethanol, followed by removing the catalyst, concentrating the solution and subjecting the concentrate to vacuum distillation to obtain oily p-(1-methylheptyloxy)phenol (IIIa-2) (30.7 g) having a b.p. of 129°-130.5° C./0.5 Torr.

후처리

  1. temperatureheating the mixture
  2. temperatureunder reflux for 4 hours
  3. distillationdistilling off most of ethanol
  4. extractionextracting with toluene
  5. washwashing with acid
  6. dry with materialalkali and water, drying
  7. concentrationconcentrating
  8. custompurifying the concentrate

출처 및 근거

ORD 기록
ord-9b2d367a034e4347893a65e31c228f54
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04751019

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