Carbon Tetrachloride → Bicyclo[3.1.1]hept-2-ene, 2-(chloromethyl)-6,6-dimethyl-

HRID 1065086Notes

Reaction equation

HRID 1065086 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]1([CH3:30])[CH:26]2[CH2:27][CH:22]1[CH2:23][CH:24]=[C:25]2[CH2:28]O.C(Cl)(Cl)(Cl)[Cl:32]>>[Cl:32][CH2:28][C:25]1[CH:26]2[CH2:27][CH:22]([CH2:23][CH:24]=1)[C:21]2([CH3:30])[CH3:20]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 10582Bicyclo[3.1.1]hept-2-ene-2-methanol, 6,6-dimethyl-HCID 11776Triphenylphosphine

Product 1

HCID 161680Bicyclo[3.1.1]hept-2-ene, 2-(chloromethyl)-6,6-dimethyl-

Procedure

A mixture of triphenylphosphine (7.87 g, 0.03 mol) and 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-methanol (3.04 g, 0.02 mol) in dry carbon tetrachloride (14.0 ml) was stirred and heated at 60° for 4.0 h. After cooling, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to afford a semi crystalline mass. This residue was triturated with n-pentane (30 ml), and the mixture was filtered. The filtrate was concentrated under reduced pressure, and the resulting oil was distilled, to afford 2-chloromethyl-6,6-dimethylbicyclo[3.1.1]hept-2-ene as a colourless oil, b.p. 32°-33°/0.2 mm Hg.

Workup

  1. temperatureheated at 60° for 4.0 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto afford a semi crystalline mass
  6. customThis residue was triturated with n-pentane (30 ml)
  7. filtrationthe mixture was filtered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. distillationthe resulting oil was distilled

Sources & evidence

ORD record
ord-e57a78eda49c488f8c389f07f04c9e20
Source dataset
uspto-grants-1982_05
Patent number
US04328234

Reaction notes

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