Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Ethyl 4,4,4-trifluoroacetoacetate | HCID 67793 | — |
| Reactant | 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol | HCID 268786 | — |
| Product | HCID 22493863 | HCID 22493863 | 38.2% |
Reaction Steps
A mixture of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ol (Intermediate 2, 4.12 g, 20.2 mmol), ethyl trifluoroacetoacetate (7.4 mL, 50.4 mmol), and H2SO4 (8 mL, 75%) was heated at 100° C. for 4 h. The mixture was poured onto ice, quenched with NaHCO3 and extracted with Et2O. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was dissolved in Et2O, a readily crystalline side product precipitated and was removed by filtration. The filtrate was concentrated to give a residue. Recrystallization of the residue gave the title compound as white crystals (2.5 g, 38%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06884820B2 |
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| Source dataset | uspto-grants-2005_04 |
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| ORD ID | ord-d958a55e74b548c38c940b8b80b847d7 |
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| Source note | uspto-grants-2005_04 |
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