Hydroquinone → HCID 131726869, compound
Reaction equation
[CH3:1][C:2](=[CH2:10])/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:11]([CH:13]=[CH2:14])=[O:12].C1(C=CC(O)=CC=1)O>>[CH:11]([C@@H:13]1[C@H:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=[C:2]([CH3:1])[CH2:10][CH2:14]1)=[O:12]Participants
Conditions
- Temperature
- 97.5 °C
Procedure
A mixture of ethyl(2E)-4-methylpenta-2,4-dienoate (8.5 g, 60.6 mmol), acrolein (5.1 g, 91 mmol) and hydroquinone (67 mg, 0.6 mmol) was heated to 95-100° C. for 24 h. The mainly cis-ethyl 6-formyl-3-methylcyclohex-2-ene-1-carboxylate was isolated by distillation (60-80° C./0.5 mm Hg) and then equilibrated with freshly activated basic alumina (−2 grams of basic alumina per gram of cis-ethyl 6-formyl-3-methylcyclohex-2-ene-1-carboxylate) in benzene as solvent (−6 mL benzene per gram of cis-ethyl 6-formyl-3-methylcyclohex-2-ene-1-carboxylate). After stirring at room temperature for 6 days, the equilibration mixture was filtered through Celite™ and the filter cake was washed with ethyl acetate. (1R/S,6R/S)-Ethyl 6-formyl-3-methylcyclohex-2-ene-1-carboxylate was then purified by distillation (65° C./15 mm Hg) as a colorless oil.
Sources & evidence
- ORD record
- ord-214017fd1e7c48008f80c8b01451fb4d
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07371747B2
Reaction notes
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