HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 257229Generated: October 31, 2026
Toluene → 2H-2,4a-Methanonaphthalene, 1,3,4,5,6,7-hexahydro-1,1,5,5-tetramethyl-, (2S)-
https://huagongshe.com/reaction/257229
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Boron trifluoride | HCID 6356 | — |
| Reactant | 4,8,8-Trimethyl-9-methylidenedecahydro-1,4-methanoazulene | HCID 289151 | — |
| Product | 2H-2,4a-Methanonaphthalene, 1,3,4,5,6,7-hexahydro-1,1,5,5-tetramethyl-, (2S)- | HCID 102562 | — |
Reaction Steps
Over a period of 30 minutes 240 g (0.79 mol) of Longifolene (1) (80% ex Indian oil of turpentine [α]D +39.4°) were dropped into a heated solution (60° C.) of 90 g toluene and 10 g (0.07 mol) BF3 -etherate. This was stirred at 100° C. for 3 hours, than cooled down to room temperature and neutralized. After drying above Na2SO4 the solvent was distilled at reduced pressure. A raw product of 198 g (of 70.2% according to GLC) remained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05260459 |
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| Source dataset | uspto-grants-1993_11 |
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| ORD ID | ord-1f7fb9a84aa243b18cebb61a6a7b71cc |
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| Source note | uspto-grants-1993_11 |
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