Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2,4-Di-tert-butylphenol | HCID 7311 | — |
| Reactant | 3,3,5-Trimethylcyclohexanone | HCID 13398 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 21224649 | HCID 21224649 | 43% |
Reaction Steps
A mixture consisting of 30.9 g (0.15 mol) of 2,4-di-tert-butylphenol and 10.5 g (0.075 mol) of 3,3,5-trimethylcyclohexanone is melted together and is then saturated, with stirring, with hydrochloric acid gas at 35° C. After 24 hours, the reaction mixture is again saturated with hydrochloric acid gas and is then stirred for 20 hours. Subsequently, the green reaction mixture is diluted with hexane and washed with water and sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated on a rotary evaporator. The residue is chromatographed over silica gel using the solvent system hexane/ethyl acetate=49:1, giving 10.6 g (43%) of 2,4-di-tert-butyl-6-(3,5,5-trimethylcyclohexen-1-yl)phenol as a thick yellowish oil (compound (106), Table 1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05932642 |
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| Source dataset | uspto-grants-1999_08 |
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| ORD ID | ord-7c16b9d8ad114247a64311ae86a82c87 |
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| Source note | uspto-grants-1999_08 |
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