Trichloroacetyl chloride → HCID 13924057, compound

HRID 569223Notes

Reaction equation

HRID 569223 reaction equation
[Cl:1][C:2]([Cl:7])(Cl)[C:3](Cl)=[O:4].P(Cl)(Cl)(Cl)=O.[CH2:13]([O:15][CH:16]([CH2:26][CH3:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH:21]1[CH2:25][CH2:24][CH:23]=[CH:22]1)[CH3:14].C(=O)(O)[O-].[Na+]>CCOCC.[Zn].[Cu]>[Cl:1][C:2]1([Cl:7])[CH:24]2[CH:25]([CH:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH:16]([O:15][CH2:13][CH3:14])[CH2:26][CH3:27])[CH2:22][CH2:23]2)[C:3]1=[O:4]

Participants

7

Reactant 4

HCID 6420Trichloroacetyl chlorideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 13924082HCID 13924082, compound

Product 1

HCID 13924057HCID 13924057, compound

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A solution containing trichloroacetyl chloride (187 g, 1.03 moles) and phosphorous oxychloride (158 g, 1.03 moles), both dissolved in 500 ml ether (1700 ml) is added dropwise to a reaction vessel containing zinc/copper couple (75 g, 1.15 moles), 3-(5-ethoxyheptyl)cyclopentene (170 g, 0.573 moles), and ether (1700 ml). After the addition is complete the reaction is refluxed for 4 hours. The reaction vessel is cooled to room temperature and the mixture neutralized by adding it to a saturated solution of sodium bicarbonate. The solution is filtered, the phases separated, and the aqueous layer is extracted with ether. The organic phases are combined and dried over anhydrous sodium sulfate. The solvent is removed under vacuum leaving a clear yellow oil. The crude product is fractionally distilled under vacuum leaving the product as a clear, colorless oil of 7,7-dichloro-4-(5-ethoxyheptyl)bicyclo [3.2.0]heptan 6-one, BP 145° C./0.3 mm.

Workup

  1. additionis added dropwise to a reaction vessel
  2. additionAfter the addition
  3. temperatureis refluxed for 4 hours
  4. filtrationThe solution is filtered
  5. customthe phases separated
  6. extractionthe aqueous layer is extracted with ether
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent is removed under vacuum
  9. customleaving a clear yellow oil
  10. distillationThe crude product is fractionally distilled under vacuum

Sources & evidence

ORD record
ord-da5f1477e5fc4e5984fd3e6494f2e109
Source dataset
uspto-grants-1988_03
Patent number
US04731458

Reaction notes

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