Ethylene Glycol → 1-(p-Chlorophenyl)cyclobutanecarboxylic acid

HRID 225171Notes

Reaction equation

HRID 225171 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]#N)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:14].[K+].C(O)C[OH:18]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([OH:18])=[O:14])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrile

Product 1

HCID 6027611-(p-Chlorophenyl)cyclobutanecarboxylic acid

Procedure

1-(4-chlorophenyl)cyclobutane nitrile (5 g) was mixed with ethylene glycol (60 ml) and 40% w/w aqueous potassium hydroxide solution (80 ml) and refluxed under argon for 18 hours. The mixture was cooled, added to ice water nd extracted with diethyl ether. The aqueous layer was acidified and the precipitate was filtered off, washed with water, dried and recrystallized from petroleum ether (b.p. 40°-60°) to give the acid as white needles mp 88°-89°, yield, 4.5 g (82%).

Workup

  1. temperaturerefluxed under argon for 18 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with diethyl ether
  4. filtrationthe precipitate was filtered off
  5. washwashed with water
  6. customdried
  7. customrecrystallized from petroleum ether (b.p. 40°-60°)

Sources & evidence

ORD record
ord-c6d3cd16ad4b42388b6b3e3f74bb8f23
Source dataset
uspto-grants-1980_11
Patent number
US04235926

Reaction notes

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