Cyclohexanone, 3,3-dimethyl- → 1-(4-Benzyloxy-phenyl)-3,3-dimethyl-cyclohexanol

HRID 237758ノート

反応式

HRID 237758 の反応式
[Mg].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:17][C:18]1([CH3:25])[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH2:19]1>BrC(Br)C.C1COCC1>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:20]2([OH:24])[CH2:21][CH2:22][CH2:23][C:18]([CH3:25])([CH3:17])[CH2:19]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 76322Cyclohexanone, 3,3-dimethyl-HCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 5462224Magnesium2 回

生成物 1

HCID 685239591-(4-Benzyloxy-phenyl)-3,3-dimethyl-cyclohexanol収率 53.4%

試薬・触媒・溶媒 2

HCID 112011,1-Dibromoethane触媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
60 °C

実験手順

In a RB flask (250 mL) was placed magnesium turnings (2.08 g, 85.9 mmol), which were stirred under vacuum without solvent overnight. To the stirred magnesium turnings was added anhydrous THF (10 mL). To the resulting mixture at 50° C. was added several drops of dibromoethane, followed by 4-benzyloxybromobenzene (11.8 g, 42.9 mmol) in 40 ml of THF. After addition was complete, the reaction mixture was heated at 60° C. for 3 hours until a brownish-grey slurry was formed. The reaction mixture was cooled in an ice-bath and 3,3-dimethyl-cyclohexanone (3.87 g, 30.67 mmol) in THF (15 mL) was added dropwise. The reaction mixture was stirred at room temperature for one hour. The solvent was removed under reduced pressure. The residue was partitioned between EtOAc/aqueous NH4Cl. The aqueous phase was extracted three times with EtOAc. The organic phase was combined and dried (Na2SO4). Silica gel chromatography (EtOAc/heptane) provided 5.08 g of 1-(4-benzyloxy-phenyl)-3,3-dimethyl-cyclohexanol as a white solid.

後処理

  1. customIn a RB flask (250 mL) was placed
  2. additionAfter addition
  3. customwas formed
  4. temperatureThe reaction mixture was cooled in an ice-bath
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was partitioned between EtOAc/aqueous NH4Cl
  7. extractionThe aqueous phase was extracted three times with EtOAc
  8. dry with materialdried (Na2SO4)

出典と根拠

ORDレコード
ord-59ab291a648c42589a51c0ae76ef90c9
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

反応ノート

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