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

HRID 1702599Notes

Reaction equation

HRID 1702599 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 acidYield 82%

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 and extracted with diethyl ether. The aqueous layer was acidified and the precipitate was filtered off, washed with water, dried and recrystallised from petroleum ether (b.p. 40°-60°) to give the acid as white needles mp 88°-9°, 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. customrecrystallised from petroleum ether (b.p. 40°-60°)

Sources & evidence

ORD record
ord-d9ed2426eee2470983865bd203271c8f
Source dataset
uspto-grants-1982_09
Patent number
US04348409

Reaction notes

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