Phenol → 4-(1-Phenylcyclohexyl)phenol

HRID 237749

반응식

HRID 237749 반응식
[C:1]1([C:7]2(O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)(=O)C.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>[C:1]1([C:7]2([C:17]3[CH:18]=[CH:19][C:14]([OH:20])=[CH:15][CH:16]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 996PhenolHCID 153191-Phenylcyclohexanol

생성물 1

HCID 15384544-(1-Phenylcyclohexyl)phenol수율 78.9%

시약·촉매·용매 2

HCID 124969952-Methylbenzenesulfonic acid hydrate촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

A mixture of 5 g (28.4 mmol) of 1-phenyl-1-cyclohexanol, 5.35 g (56.8 mmol) of phenol and 250 mg (1.32 mmol) of toluenesulfonic acid monohydrate was stirred at 85° C. under nitrogen atmosphere for 4 hours. The material was allowed to cool to room temperature, diluted with ethyl acetate, washed with saturated sodium bicarbonate, water and brine. The resulting solution was dried (Na2SO4), filtered and concentrated to a white solid which was heated under high vacuum to remove residual phenol. The resulting residue was purified by flash chromatography on silica gel, eluting with methanol/dichloromethane to provide 5.64 g (22.4 mmol) of 4-(1′-(phenyl)cyclohexyl)phenol.

후처리

  1. temperatureto cool to room temperature
  2. washwashed with saturated sodium bicarbonate, water and brine
  3. dry with materialThe resulting solution was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a white solid which
  6. temperaturewas heated under high vacuum
  7. customto remove residual phenol
  8. customThe resulting residue was purified by flash chromatography on silica gel
  9. washeluting with methanol/dichloromethane

출처 및 근거

ORD 기록
ord-03f4c38d3ae34542b0c677855a714989
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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