Trichloroacetyl chloride → 7,7-Dichloro-4-heptylbicyclo[3.2.0]heptan-6-one

HRID 569224Notes

Reaction equation

HRID 569224 reaction equation
[Cl:1][C:2]1([Cl:20])[CH:8]2[CH:4]([CH:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH:13](OCC)[CH2:14][CH3:15])[CH2:6][CH2:7]2)[C:3]1=[O:19].C(C1CCC=C1)CCCCCC.ClC(Cl)(Cl)C(Cl)=O.P(Cl)(Cl)(Cl)=O>CCOCC.[Zn].[Cu]>[Cl:1][C:2]1([Cl:20])[CH:8]2[CH:4]([CH:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:6][CH2:7]2)[C:3]1=[O:19]

Participants

7

Reactant 4

HCID 6420Trichloroacetyl chlorideHCID 24813Phosphorus oxychlorideHCID 13924057HCID 13924057, compoundHCID 139240793-Heptylcyclopentene

Product 1

HCID 139240677,7-Dichloro-4-heptylbicyclo[3.2.0]heptan-6-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 10290809Zinc copper coupleSolvent

Procedure

The next procedure followed is that of the preceding Example for the preparation of 7,7-dichloro-4-(5-ethoxyheptyl)bicyclo [3.2.0] heptan-6-one, substituting 3-heptylcyclopentene (49 g, 0.30 moles) diluted in ether (490 ml), trichloroacetyl chloride (97 g, 0.53 moles) and phosphorous oxychloride (81 g, 0.53 moles) both diluted with ether (150 ml), zinc/copper couple (30 g, 0.59 moles) were used. The crude product is submitted to short path distillation and subsequently fractionally distilled under reduced pressure, leaving a clear, colorless oil of 7,7-dichloro-4-heptylbicyclo[3.2.0]heptan-6-one (20.6 g, 0.075 moles), BP 115° C./0.22 mm.

Workup

  1. distillationThe crude product is submitted to short path distillation
  2. distillationsubsequently fractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-b469a3b2863f4883ba8931831bcf820d
Source dataset
uspto-grants-1988_03
Patent number
US04731458

Reaction notes

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