Isopropanol → 1-(1-Chloroethenyl)cyclohexanecarboxylic acid

HRID 894361Notes

Reaction equation

HRID 894361 reaction equation
[Cl:1][C:2]([C:4]1([C:10]([O:12]C)=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[CH2:3].[OH-].[K+].C(O)(C)C>O>[Cl:1][C:2]([C:4]1([C:10]([OH:12])=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[CH2:3]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 20575458HCID 20575458, compound

Product 1

HCID 205754641-(1-Chloroethenyl)cyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

13 g of methyl 1-(1'-chlorovinyl)-cyclohexylcarboxylate were refluxed with 4 g of potassium hydroxide, 20 cm3 of isopropanol and 10 cm3 of water for 6 hours. A solid was obtained by evaporating off the alcohol and this solid was dissolved in water. The basic aqueous solution was washed with ether and then acidified with dilute hydrochloric acid. The expected 1-(1'-chlorovinyl)-1-cyclohexyl-carboxylic acid was extracted with ether. After evaporating off the solvent, the product was purified by recrystallisation from pentane and colourless crystals were obtained.

Workup

  1. customA solid was obtained
  2. customby evaporating off the alcohol
  3. dissolutionthis solid was dissolved in water
  4. washThe basic aqueous solution was washed with ether
  5. extractionThe expected 1-(1'-chlorovinyl)-1-cyclohexyl-carboxylic acid was extracted with ether
  6. customAfter evaporating off the solvent
  7. customthe product was purified by recrystallisation from pentane
  8. customcolourless crystals were obtained

Sources & evidence

ORD record
ord-29ae118ece3b4aacb45266717fbc0c68
Source dataset
uspto-grants-1981_08
Patent number
US04283420

Reaction notes

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