Phenol → 4-(1-Phenylcyclohexyl)phenol

HRID 237749

反応式

HRID 237749 の反応式
[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

参加物

5

反応物 2

HCID 996PhenolHCID 153191-Phenylcyclohexanol

生成物 1

HCID 15384544-(1-Phenylcyclohexyl)phenol収率 78.9%

試薬・触媒・溶媒 2

HCID 124969952-Methylbenzenesulfonic acid hydrate触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-03f4c38d3ae34542b0c677855a714989
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

関連ノート

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