4-Methylcyclohex-1-ene-1-carboxylic acid → 4-Methyl-3-cyclohexene-1-carboxylic Acid

HRID 1758474Notes

Reaction equation

HRID 1758474 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH2:3]1>O>[CH3:1][C:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH:3]=1

Participants

3

Reactant 1

HCID 2193894-Methylcyclohex-1-ene-1-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reaction: ##STR17## 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 NOAH 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: ##STR18## as confirmed by NMR and IR analysis.

Workup

  1. customReaction
  2. custom##STR17## into 1 liter reaction flask
  3. customequipped with stirrer
  4. temperaturereflux condenser
  5. temperatureheating mantle
  6. extractionextracted with 1 volume of diethyl ether
  7. extractionextracted with diethyl ether
  8. washThe diethyl ether extracts are washed with saturated sodium chloride solution
  9. customthe ether is evaporated

Sources & evidence

ORD record
ord-5dab23bf16ec40ff971bd462f8134ed1
Source dataset
uspto-grants-1983_02
Patent number
US04374123

Reaction notes

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