Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | p-Menth-4(8)-en-3-one | HCID 6988 | — |
| Reactant | Trimethylaluminum | HCID 16682925 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 228327 | HCID 228327 | 70% |
Reaction Steps
28.5 ml (33 mmol) of trimethylaluminum as 10% solution in toluene is instilled in 4.56 g (30 mmol) of 2-isopropylidene-5-methyl-cyclohexan-1-one (pulegone) and 214.5 mg (1.5 mmol) of CuBr in 30 ml of ethyl acetate. The reaction solution is stirred for 1 more hour at 25° C. For hydrolysis, 2 ml of water is carefully added and stirred for 15 more minutes. The inorganic solid is suctioned off, rewashed with ethyl acetate and the solution is concentrated by evaporation in a vacuum. Distillation of the crude product at 120° C./6 torr yields 3.4 g of 2-tert-butyl-5-methyl-cyclohexanone (70% of theory) as a mixture of isomers.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05908945 |
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| Source dataset | uspto-grants-1999_06 |
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| ORD ID | ord-068c91c5f7ec4164a6b28906db4574e9 |
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| Source note | uspto-grants-1999_06 |
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