Ethylene Glycol → 1-(1-Naphthyl)cyclopropanecarboxylic acid

HRID 440533Notes

Reaction equation

HRID 440533 reaction equation
[C:1]1([C:11]2([C:14]#N)[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-:16].[K+].C(O)C[OH:20]>O>[C:1]1([C:11]2([C:14]([OH:20])=[O:16])[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 122186561-(1-Naphthyl)cyclopropanecarbonitrile

Product 1

HCID 122764501-(1-Naphthyl)cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 1-(1-naphthyl)cyclopropanecarbonitrile (60.7 g, prepared in a similar manner to that described in Example N9) and 10% aqueous potassium hydroxide solution was stirred and heated under reflux for 16 hours. Ethylene glycol (250 ml) was added and the mixture was heated under reflux for 5 hours. Each time complete solution was achieved, further water was added to cloud point. Water (500 ml) was added and the mixture was allowed to stand for 16 hours. The resulting solid was removed by filtration. The filtrate was diluted with water (800 ml), filtered, and the filtrate acidified by addition of dilute hydrochloric acid. The resulting solid was collected by filtration, washed with water and dried in air, yielding 1-(1-naphthyl)cyclopropane carboxylic acid (25.9 g).

Workup

  1. customprepared in a similar manner to that
  2. temperatureheated
  3. temperatureunder reflux for 16 hours
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 5 hours
  6. customThe resulting solid was removed by filtration
  7. additionThe filtrate was diluted with water (800 ml)
  8. filtrationfiltered
  9. additionthe filtrate acidified by addition of dilute hydrochloric acid
  10. filtrationThe resulting solid was collected by filtration
  11. washwashed with water
  12. customdried in air

Sources & evidence

ORD record
ord-bde11354a6bf43ecaf5bd8a7888f476b
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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