Carbon Tetrachloride → Farnesylacetyl chloride

HRID 1659292Notes

Reaction equation

HRID 1659292 reaction equation
[CH2:1]([CH2:16][C:17]([OH:19])=O)[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:40]>>[CH2:1]([CH2:16][C:17]([Cl:40])=[O:19])[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4]

Participants

4

Reactant 3

HCID 5943Carbon Tetrachloride2×HCID 11776TriphenylphosphineHCID 1524704,8,12-Tetradecatrienoic acid, 5,9,13-trimethyl-

Product 1

HCID 54440908Farnesylacetyl chloride

Procedure

A three-necked flask equipped with a stirrer, a reflux condenser and a thermometer was charged with 132 g of farnesylacetic acid, 140 g of triphenylphosphine and 500 ml of carbon tetrachloride, and the contents were heated under reflux of carbon tetrachloride for 4 hours. The reaction mixture was filtered to remove a formed solid matter, the carbon tetrachloride distilled off, 500 ml of n-hexane added, the mixture ice-cooled and the crystalline precipitate filtered off. The n-hexane was then distilled off, leaving 146 g of crude farnesylacetyl chloride.

Workup

  1. customA three-necked flask equipped with a stirrer, a reflux condenser
  2. temperaturethe contents were heated
  3. filtrationThe reaction mixture was filtered
  4. customto remove a formed solid matter
  5. distillationthe carbon tetrachloride distilled off
  6. addition500 ml of n-hexane added
  7. temperaturethe mixture ice-cooled
  8. filtrationthe crystalline precipitate filtered off
  9. distillationThe n-hexane was then distilled off

Sources & evidence

ORD record
ord-85a81f671eb14189967914cf22832e99
Source dataset
uspto-grants-1981_12
Patent number
US04303588

Reaction notes

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