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

HRID 72938

반응식

HRID 72938 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 608867294-(2-Hydroxy-2-methyl-propoxy)benzonitrile수율 94%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5d116b454f9a4d428593fff5a53f2942
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828996B2

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