Phenol → 4-(1-Phenylcyclohexyl)phenol

HRID 70728

반응식

HRID 70728 반응식
[C:1]1([C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.B(F)(F)F.OP(O)(O)=O>ClCCl>[C:1]1([C:7]2([C:16]3[CH:17]=[CH:18][C:13]([OH:19])=[CH:14][CH:15]=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

6

반응물 4

HCID 996PhenolHCID 1004Phosphoric AcidHCID 6356Boron trifluorideHCID 130431-Phenylcyclohexene

생성물 1

HCID 15384544-(1-Phenylcyclohexyl)phenol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

1-Phenyl-1-cyclohexene (1 g, 6.3 mmol), phenol (1.5 g, 15.9 mmol) and BF3.H3PO4 (0.05 mL) were mixed and shaken at 80° C. overnight. Dichloromethane (30 mL) was added and the organic phase was washed with saturated NaHCO3 (aq.) (2×10 mL), dried (Na2SO4) and concentrated. The title compound was crystallised from a mixture of methanol and water. Yield: 1040 mg. 1H NMR (400 MHz, CDCl3): δ 7.28-7.25 (m, 4H), 7.16-7.10 (m, 3H), 6.75-6.70 (m, 2H), 4.51 (br. s, 1H), 2.28-2.22 (m, 4H), 1.60-1.52 (m, 4H), 1.52-1.45 (m, 2H). 13C NMR (100 MHz, CDCl3): δ 153.25, 149.15, 141.22, 128.63, 128.39, 127.29, 125.55, 115.21, 45.89, 37.50, 26.63, 23.14. LC-MS purity (UV/MS): 100/100%, Rt 5.07 min, M−1: 251.62.

후처리

  1. washthe organic phase was washed with saturated NaHCO3 (aq.) (2×10 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe title compound was crystallised from a mixture of methanol and water

출처 및 근거

ORD 기록
ord-4579ee66f8f149bfb026a47061283677
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822548B2

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