Water → 4-(2-Hydroxy-2-methyl-propoxy)benzonitrile

HRID 72938

反応式

HRID 72938 の反応式
Cl[CH2:2][C:3]([CH3:6])([OH:5])[CH3:4].[OH:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[OH:5][C:3]([CH3:6])([CH3:4])[CH2:2][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 684091-Chloro-2-methylpropan-2-ol

生成物 1

HCID 608867294-(2-Hydroxy-2-methyl-propoxy)benzonitrile収率 94%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1-chloro-2-methyl-propan-2-ol (10 mL), 4-hydroxybenzonitrile (2.0 g, 16.8 mmol), potassium carbonate (9.3 g, 67.3 mmol), water (6 mL) and ethanol (60 mL) was heated at 80° C. overnight. The reaction mixture was cooled, concentrated in vacuo and residue was diluted with ether (200 mL) and filtered. The filtrate was washed with water (50 mL) and brine solution (50 mL). The organics were separated and dried over MgSO4 and purified by silica gel column chromatography using 0-100% EtOAc/DCM as eluent to give 4-(2-hydroxy-2-methyl-propoxy)benzonitrile (3.0 g, 94%) as a yellow solid. ESI-MS m/z calc. 191.1. Found 192.3 (M+1)+; Retention time: 1.05 minutes (3 min run).

後処理

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo and residue
  3. additionwas diluted with ether (200 mL)
  4. filtrationfiltered
  5. washThe filtrate was washed with water (50 mL) and brine solution (50 mL)
  6. customThe organics were separated
  7. dry with materialdried over MgSO4
  8. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-5d116b454f9a4d428593fff5a53f2942
出典データセット
uspto-grants-2014_09
特許番号
US08828996B2

関連ノート

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