Toluene → 2H-2,4a-Methanonaphthalene, 1,3,4,5,6,7-hexahydro-1,1,5,5-tetramethyl-, (2S)-

HRID 21897Notes

Reaction equation

HRID 21897 reaction equation
[CH3:1][C:2]1([CH3:15])[CH:8]2[CH:9]3[CH2:12][CH2:13][CH:7]2[C:6](C)([C:10]3=[CH2:11])[CH2:5][CH2:4][CH2:3]1.B(F)(F)F.[C:20]1(C)C=CC=CC=1>>[CH3:15][C:2]1([CH3:1])[C:7]23[CH2:8][CH:9]([C:10]([CH3:11])([CH3:20])[C:6]2=[CH:5][CH2:4][CH2:3]1)[CH2:12][CH2:13]3

Participants

4

Reactant 3

HCID 1140TolueneHCID 6356Boron trifluorideHCID 2891514,8,8-Trimethyl-9-methylidenedecahydro-1,4-methanoazulene

Product 1

HCID 1025622H-2,4a-Methanonaphthalene, 1,3,4,5,6,7-hexahydro-1,1,5,5-tetramethyl-, (2S)-

Conditions

Temperature
100 °C

Procedure

Over a period of 30 minutes 240 g (0.79 mol ) of Longifolene (1) (80% ex Indian oil of turpentine [a]D=+39.4°) were dropped into a heated solution (60 ° C.) of 90 g toluene and 10 g (0.07 tool ) 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.

Workup

  1. temperaturethan cooled down to room temperature
  2. dry with materialAfter drying above Na2SO4 the solvent
  3. distillationwas distilled at reduced pressure

Sources & evidence

ORD record
ord-1e84889c3c734dea9caec48a41531df3
Source dataset
uspto-grants-1995_06
Patent number
US05426095

Reaction notes

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