Methanol → 3-methoxycarbonylcyclohexa-1,4-diene
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureThe reaction was heated
- temperatureto reflux in air for 1 h
- temperaturecooled
- extractionextracted with ether (3×50 ml)
- washThe combined ether layers were washed with 5% Na[HCO3] solution (50 ml) and saturated NaCl solution (50 ml)
- dry with materialdried over MgSO4
- customThe ether was removed on the rotary evaporator
- customto leave a colourless oil which
- 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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