p-Toluenesulfonic acid → (4,4-Diethoxycyclohexylmethoxymethyl)benzene

HRID 1518072ノート

反応式

HRID 1518072 の反応式
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14]C(=O)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:20]([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C(O)C>[CH2:25]([O:24][C:20]1([O:21][CH2:22][CH3:23])[CH2:12][CH2:11][CH:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:15][CH2:14]1)[CH3:26]

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 31214Ethyl orthoformateHCID 10443381Cyclohexanone, 4-[(phenylmethoxy)methyl]-

生成物 1

HCID 57617622(4,4-Diethoxycyclohexylmethoxymethyl)benzene

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-Benzyloxymethylcyclohexanone (168 g, 0.77 mol) is dissolved in ethanol (2000 mL), and then triethylorthoformate (350 mL) and p-toluenesulfonic acid (13.3 g) are added. The resulting mixture is stirred and refluxed for 6 hours. After addition of triethylamine (10.5 mL) at room temperature, the mixture is concentrated (500 mL). After addition of sat. NaHCO3 aq., the resulting mixture is extracted with EtOAc. The water layer is extracted with EtOAc and the combined organic layer is washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude mixture is purified by short pad silica gel column chromatography to afford (4,4-diethoxycyclohexylmethoxymethyl)benzene.

後処理

  1. temperaturerefluxed for 6 hours
  2. concentrationthe mixture is concentrated (500 mL)
  3. additionAfter addition of sat. NaHCO3 aq.
  4. extractionthe resulting mixture is extracted with EtOAc
  5. extractionThe water layer is extracted with EtOAc
  6. washthe combined organic layer is washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude mixture is purified by short pad silica gel column chromatography

出典と根拠

ORDレコード
ord-e1a349cacaae402aae1f4980f0fe9ecd
出典データセット
uspto-grants-2012_07
特許番号
US08232403B2

反応ノート

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