Water → 1-Phenylcyclobutanecarboxylic acid

HRID 1408524Notes

Reaction equation

HRID 1408524 reaction equation
[C:1]1([C:7]2([C:11]#N)[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:13].[K+].C1(C)C=CC=CC=1.[OH2:22]>C(O)CO>[C:1]1([C:7]2([C:11]([OH:22])=[O:13])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 14797Potassium HydroxideHCID 844001-Phenylcyclobutanecarbonitrile

Product 1

HCID 2771711-Phenylcyclobutanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
160 °C

Procedure

Intermediate 60 (2.6 g, 16.54 mmol) was dissolved in ethyleneglycol and added potassium hydroxide (5.6 g, 99.2 mmol). This mixture was heated to 160° C. for 2 h. After two hours reaction mixture was cooled to rt and toluene and water were added. Aqueous layer separated and acidified with HCl and pH adjusted to 4. Aqueous layer extracted with ethyl acetate and ethyl acetate layer was dried on anhydrous sodium sulphate. Ethyl acetate removed on rotavapour to obtain the title compound (930 mg) as a white solid.

Workup

  1. customAfter two hours reaction mixture
  2. temperaturewas cooled to rt
  3. customAqueous layer separated
  4. extractionAqueous layer extracted with ethyl acetate and ethyl acetate layer
  5. dry with materialwas dried on anhydrous sodium sulphate
  6. customEthyl acetate removed on rotavapour

Sources & evidence

ORD record
ord-71aa019d0ba2401fabddd4773ae55d49
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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