Boron trifluoride → 4,4,8-Trimethyl-9-methylene-bicyclo[3.3.1]nonan-6-one

HRID 1283365Notes

Reaction equation

HRID 1283365 reaction equation
[CH3:1][C:2]1[CH:3]([C:10](=[O:14])/[CH:11]=[CH:12]/[CH3:13])[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH:7]=1.B(F)(F)F>C1C=CC=CC=1.CCOCC>[CH3:9][C:4]1([CH3:8])[CH:3]2[C:2](=[CH2:1])[CH:7]([CH:12]([CH3:13])[CH2:11][C:10]2=[O:14])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 6356Boron trifluorideHCID 5366077(E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one

Product 1

HCID 233380624,4,8-Trimethyl-9-methylene-bicyclo[3.3.1]nonan-6-one

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,6,6-trimethyl-1-crotonoyl-2-cyclohexene (1.0 g.) in a mixture of benzene and ether (10 ml.) was heated at ca. 80° in the presence of a catalytic amount of a saturated solution of BF3 in ether. The course of the reaction was followed by v.p.c. analysis. Three hours were usually necessary for converting the starting material into the bicyclic compound.

Workup

  1. customThree hours

Sources & evidence

ORD record
ord-3d250ec452554760877bb3f66f537124
Source dataset
uspto-grants-1976_08
Patent number
US03975310

Reaction notes

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