Methanol → 3-methoxycarbonylcyclohexa-1,4-diene

HRID 353279Notes

Reaction equation

HRID 353279 reaction equation
OS(O)(=O)=O.[C:6]([OH:14])(=[O:13])[CH:7]1[CH:12]=[CH:11][CH2:10][CH:9]=[CH:8]1.[CH3:15]O>O>[CH3:15][O:13][C:6]([CH:7]1[CH:12]=[CH:11][CH2:10][CH:9]=[CH:8]1)=[O:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 78522Cyclohexa-2,5-diene-1-carboxylic acid

Product 1

HCID 110624513-methoxycarbonylcyclohexa-1,4-diene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated H2SO4 (1 ml) was added to a solution of 1,4-dihydrobenzoic acid (3 g, 23.97 mmol) in freshly dried methanol (10 ml). The reaction was heated to reflux in air for 1 h, cooled, poured into H2O (25 ml) and extracted with ether (3×50 ml). The combined ether layers were washed with 5% Na[HCO3] solution (50 ml) and saturated NaCl solution (50 ml) and dried over MgSO4. The ether was removed on the rotary evaporator to leave a colourless oil which was used without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux in air for 1 h
  3. temperaturecooled
  4. extractionextracted with ether (3×50 ml)
  5. washThe combined ether layers were washed with 5% Na[HCO3] solution (50 ml) and saturated NaCl solution (50 ml)
  6. dry with materialdried over MgSO4
  7. customThe ether was removed on the rotary evaporator
  8. customto leave a colourless oil which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-4b9adb23a35e42bebf946fb66ec1cf8a
Source dataset
uspto-grants-2004_06
Patent number
US06750251B2

Reaction notes

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