Carbon Tetrachloride → 4-Bromo-6,6,6-trichloro-3,3-dimethylhexanoic acid

HRID 1701664Notes

Reaction equation

HRID 1701664 reaction equation
[CH3:1][C:2]([CH3:9])([CH:7]=[CH2:8])[CH2:3][C:4]([OH:6])=[O:5].[Br:10]C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:33]([Cl:37])(Cl)([Cl:35])[Cl:34]>>[Br:10][CH:7]([CH2:8][C:33]([Cl:37])([Cl:35])[Cl:34])[C:2]([CH3:9])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6383BromotrichloromethaneHCID 7187Benzoyl PeroxideHCID 106304993,3-Dimethylpent-4-enoic acid

Product 1

HCID 233480094-Bromo-6,6,6-trichloro-3,3-dimethylhexanoic acid

Procedure

A mixture of 3,3-dimethypent-4-enoic acid (18.2 g.), carbon tetrachloride (100 ml.), bromotrichloromethane (57.0 g.) and benzoyl peroxide (0.15 g.) was refluxed under a nitrogen atmosphere for 72 hours after which the volatile portion was removed by evaporation under reduced pressure. The residue was recrystallised from petroleum ether (boiling range 80° to 100° C.) to yield 4-bromo-3,3-dimethyl-6,6,6-trichlorohexanoic acid, m.p. 123°-124° C.

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere for 72 hours after which the volatile portion
  2. customwas removed by evaporation under reduced pressure
  3. customThe residue was recrystallised from petroleum ether (boiling range 80° to 100° C.)

Sources & evidence

ORD record
ord-a3580cc5115441b69831d3b01dab24ae
Source dataset
uspto-grants-1980_03
Patent number
US04195033

Reaction notes

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