3-Isopropenyl-1-methyl-2-methylenecyclopentan-1-ol → 2-(2-Formyl-3-methyl-2-butenyl)-3-isopropenyl-1-methyl-cyclopent-1-ene
Reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][C:6]([CH3:10])(O)[C:5]1=[CH2:11])([CH3:3])=[CH2:2].C[O:13][CH:14](OC)[CH2:15][C:16]([CH3:18])=[CH2:17].Cl.N1C=CC=CC=1>CCOCC>[CH:14]([C:15](=[C:16]([CH3:18])[CH3:17])[CH2:11][C:5]1[CH:4]([C:1]([CH3:3])=[CH2:2])[CH2:8][CH2:7][C:6]=1[CH3:10])=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 7.6 g of 3-isopropenyl-1-methyl-2-methylene-cyclopentan-1-ol and 8.1 g of 1,1-dimethoxy-3-methyl-3-butene was heated under nitrogen in an oil bath of 100° C for 15 hours in the presence of 100 mg of freshly prepared dry pyridine hydrochloride with continuous removal of the methanol formed. The mixture was then heated for 7 hours to 150° C and finally poured on to a mixture of ice and ether. The ethereal phase was washed with bicarbonate solution and water, dried with anhydrous magnesium sulphate and concentrated under reduced pressure. After distillation of the oily crude product, there were obtained 6.5 g of 2-(2-formyl-3-methyl-2-butenyl)-3-isopropenyl-1-methyl-cyclopent-1-ene; boiling point 0.003 about 80° C; nD20 = 1.5148; IRfilm : νmax = 3100, 2780, 1675, 1635, 1440, 1375, 1155, 1060 and 895 cm-1. The compound has a woody, floral, fruitily sweetish fragrance.
Workup
- customwith continuous removal of the methanol
- customformed
- temperatureThe mixture was then heated for 7 hours to 150° C
- washThe ethereal phase was washed with bicarbonate solution and water
- dry with materialdried with anhydrous magnesium sulphate
- concentrationconcentrated under reduced pressure
- distillationAfter distillation of the oily crude product
Sources & evidence
- ORD record
- ord-44348f00c4174f4089b0cfd032aac7ce
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04031132
Reaction notes
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