Potassium Carbonate → 3-(Benzyloxy)-2,2-dimethylpropanoic acid

HRID 17315Notes

Reaction equation

HRID 17315 reaction equation
[CH2:1]([O:8][CH2:9][C:10](C)([CH3:13])[C:11]#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[C:17](=[O:20])([O-])[O-:18].[K+].[K+]>CO>[CH2:1]([O:8][CH2:9][C:10]([CH3:13])([CH3:11])[C:17]([OH:18])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 542383773-Benzyloxy-2,2-dimethylpropionitrile

Product 1

HCID 134782883-(Benzyloxy)-2,2-dimethylpropanoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

3-Benzyloxy-2,2-dimethylpropionitrile (2.0 g, 10.6 mmol), potassium hydroxide (31.2 g, 86%, 479 mmol) and potassium carbonate (1.13 g, 82 mmol) were dissolved in methanol (340 ml), concentrated under reduced pressure. The resulting residue was heated at 140° C. (bath temperature) under nitrogen atmosphere, and stirred for 22 hours. The reaction mixture was dissolved in water, cooled in an ice-water bath, followed by controlling at pH of 1 with hydrochloric acid (36%) added thereto. The organic matter was extracted with diethyl ether, washed with saturated brine, dried on anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure to obtain the entitled compound (2.18 g, 99%) as a colorless solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe reaction mixture was dissolved in water
  3. temperaturecooled in an ice-water bath
  4. additionadded
  5. extractionThe organic matter was extracted with diethyl ether
  6. washwashed with saturated brine
  7. dry with materialdried on anhydrous magnesium sulfate
  8. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-94a05bc412a44b5f94530ad2efa58759
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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