Sodium Hydroxide → 4-Methyl-3-cyclohexene-1-carboxylic Acid

HRID 2166859Notes

Reaction equation

HRID 2166859 reaction equation
[OH-].[Na+].[CH3:3][CH:4]1[CH2:9][CH2:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6][CH2:5]1>O>[CH3:3][C:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=[O:11])[CH2:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2193894-Methylcyclohex-1-ene-1-carboxylic acid

Product 1

HCID 203504-Methyl-3-cyclohexene-1-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 1 liter reaction flask equipped with stirrer, thermometer reflux condenser and heating mantle is placed 100 ml anhydrous methyl, 1.25 moles (100 grams) of 50% aqueous NaOH solution, 100 ml water and 154 grams (1 mole) of the methyl ester of 4-methyl-cyclohexene-1-carboxylic acid. The reaction mass is stirred for a period of 5 hours at room temperature and then extracted with 1 volume of diethyl ether. The aqueous layer is set aside with 10% hydrochloric acid and extracted with diethyl ether. The diethyl ether extracts are washed with saturated sodium chloride solution and the ether is evaporated yielding 100.5 grams of solid melting at 95° C. This material is the carboxylic acid having the structure: ##STR42## as confirmed by NMR and IR analysis.

Workup

  1. customInto 1 liter reaction flask
  2. customequipped with stirrer, thermometer reflux condenser
  3. temperatureheating mantle
  4. extractionextracted with 1 volume of diethyl ether
  5. extractionextracted with diethyl ether
  6. washThe diethyl ether extracts are washed with saturated sodium chloride solution
  7. customthe ether is evaporated

Sources & evidence

ORD record
ord-dcb04eac26a54c1da2d8cb573d4e3f88
Source dataset
uspto-grants-1983_06
Patent number
US04390434

Reaction notes

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