2-Methoxypropene → 4-(5-Isopropenyl-2-methyl-1-cyclopenten-1-yl)-2-butanone
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][C:14]([CH3:16])=[CH2:15]>P(=O)(O)(O)O>[C:1]([CH:4]1[CH2:8][CH2:7][C:6]([CH3:10])=[C:5]1[CH2:11][CH2:15][C:14](=[O:13])[CH3:16])([CH3:3])=[CH2:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
15 drops of 85% phosphoric acid were added to a mixture, cooled in a laboratory autoclave, of 76 g of 3-isopropenyl-1-methyl-2-methylene-cyclopentan-1-ol and 120 g of isopropenyl methyl ether. After gassing with nitrogen, the autoclave was brought, in an oil bath of 180° C, to an internal temperature of 150° C and held at this temperture until a distinct drop in pressure occurred (about 50-75 minutes). The reaction mixture was quenched by intensive cooling, treated with solid potassium hydroxide and concentrated under reduced pressure on a rotary evaporator. By fractional distillation over solid potassium hydroxide there were obtained 58 g (60%) of 3-isopropenyl-1-methyl-2-(3-oxobutyl)-cyclopent-1-ene; boiling point 0.01 = 69°-72° C; nD20 = 1.4836. The compound has a woody, camphoraceous, ionone-like fragrance.
Workup
- customthe autoclave was brought, in an oil bath of 180° C, to an internal temperature of 150° C
- custom(about 50-75 minutes)
- customThe reaction mixture was quenched by intensive cooling
- additiontreated with solid potassium hydroxide
- concentrationconcentrated under reduced pressure on a rotary evaporator
- distillationBy fractional distillation over solid potassium hydroxide there
Sources & evidence
- ORD record
- ord-047948aa7aa94d1389a8a08a24c3a8c0
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04031132
Reaction notes
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