Water → HCID 65453727, compound

HRID 555449Notes

Reaction equation

HRID 555449 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:11].Cl[CH2:13][C:14]([CH3:17])([OH:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[OH:16][C:14]([CH3:17])([CH3:15])[CH2:13][O:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([C:6]#[N:7])=[CH:8][C:9]=1[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 201763,5-Dimethyl-4-hydroxybenzonitrileHCID 684091-Chloro-2-methylpropan-2-ol

Product 1

HCID 65453727HCID 65453727, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-hydroxy-3,5-dimethylbenzonitrile (2.00 g, 13.5 mmol) and 1-chloro-2-methyl propan-2-ol (8.85 g, 81.5 mmol) in ethanol (50 mL) was added potassium carbonate (7.5 g, 54 mmol) and water (5 mL). The reaction mixture was stirred at reflux for 24 h and cooled to room temperature. The precipitated solid was filtered off and washed with water. The solid was dissolved in ethyl acetate (100 mL), washed with water (50 mL), brine (50 mL), and dried over anhydrous Na2SO4. Removal of solvent gave 4-(2-hydroxy-2-methylpropoxy)-3,5-dimethyl benzonitrile (2.9 g, 97%) as a white solid.

Workup

  1. temperatureat reflux for 24 h
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with water
  4. dissolutionThe solid was dissolved in ethyl acetate (100 mL)
  5. washwashed with water (50 mL), brine (50 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-178aa6449e104ba6bd06c0c1333b2309
Source dataset
uspto-grants-2011_11
Patent number
US08053440B2

Reaction notes

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