Sodium Hydroxide → 2,4,4-Trimethyl-1-cyclohexene-1-carboxylic acid

HRID 1413231Notes

Reaction equation

HRID 1413231 reaction equation
[CH3:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH2:4][C:3]=1[C:10]([O:12]C)=[O:11].[OH-].[Na+]>>[CH3:1][C:2]1[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5][CH2:4][C:3]=1[C:10]([OH:12])=[O:11]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 11116685HCID 11116685, compound

Product 1

HCID 110950262,4,4-Trimethyl-1-cyclohexene-1-carboxylic acidYield 66%

Procedure

Methyl 2,4,4-trimethyl-1-cyclohexene-1-carboxylate (0.5 g; 2.75 m. moles) was added to 8% aqueous sodium hydroxide solution (5 ml) and the mixture was heated under reflux for a period of 24 hours. The solution was washed with light petroleum (b.p. 60°-80° C.), acidified with dilute hydrochloric acid and extracted three times with ether. The combined extracts were dried (MgSO4) and evaporated to give a crystalline product (0.373 g; 82%) which was recrystallized from aqueous methanol to give 2,4,4-trimethyl-1-cyclohexene-1-carboxylic acid (0.3 g; 66%), m.p. 108°-110° C., (N.M.R.: δ0.92 (s,6,CH3 --C--CH3), 2.05 (b,3,C=C--CH3)).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for a period of 24 hours
  3. washThe solution was washed with light petroleum (b.p. 60°-80° C.)
  4. extractionextracted three times with ether
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customevaporated
  7. customto give a crystalline product (0.373 g; 82%) which
  8. customwas recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-28d1be933acd4602aca4c826cad920f3
Source dataset
uspto-grants-1981_02
Patent number
US04249015

Reaction notes

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