四氧化硫 → 4-Fluoro-2-(1-methylcyclohexyl)phenol

HRID 383413

反应方程式

HRID 383413 反应方程式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1(O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.S(=O)(=O)(O)O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:10]2([CH3:9])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:3]=1

参与物

5

反应物 3

HCID 1118四氧化硫HCID 97324-氟苯酚HCID 115501-甲基环己醇

产物 1

HCID 593949974-Fluoro-2-(1-methylcyclohexyl)phenol

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

4-Fluorophenol (41.8 g, 373 mmol) and 1-methylcyclohexanol (63.8 g, 560 mmol) dissolved in 600 mL of dried CH2Cl2, were treated with concentrated sulfuric acid (98%, 22.3 mL, 418 mmol). The mixture was stirred at room temperature for 50 hours. The reaction mixture was then extracted by CH2Cl2 (250 mLx3). The organic layer was washed with saturated a.q NaHCO3., dried over MgSO4, and evaporated under vacuum. The residue was purified by column chromatography on silica gel to give 4-fluoro-2-(1-methylcyclohexyl)phenol as a dark green oil—47.6 g. 1H NMR (400 MHz, CDCl3) δ 7.00 (dd, J=3.2, 11.2 Hz, 1H), 6.76-6.71 (m, 1H), 6.62-6.59 (m, 1H), 5.27 (brs, 1H), 2.13-2.07 (M, 2H), 1.70-1.37 (m, 8H), 1.32 (s, 3H).

后处理

  1. extractionThe reaction mixture was then extracted by CH2Cl2 (250 mLx3)
  2. washThe organic layer was washed with saturated a.q NaHCO3
  3. dry with material, dried over MgSO4
  4. customevaporated under vacuum
  5. customThe residue was purified by column chromatography on silica gel

来源与证据

ORD记录
ord-03f96806035348698365e249e47fb222
来源数据集
uspto-grants-2013_02
专利号
US08367660B2

关联笔记

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