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

HRID 713023Notes

Reaction equation

HRID 713023 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-94db92e7893b40709b23e977703f0b5d
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

Loading…