Trichloroacetyl chloride → 3-((Benzyloxy)methyl)cyclobutanone

HRID 1401753Notes

Reaction equation

HRID 1401753 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]=[CH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:13](Cl)(Cl)[C:14](Cl)=[O:15].P(Cl)(Cl)(Cl)=O>C(O)(=O)C.C(OCC)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.[Zn]>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:13][C:14](=[O:15])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 24813Phosphorus oxychlorideHCID 84542Allyl benzyl ether

Product 1

HCID 118198503-((Benzyloxy)methyl)cyclobutanone

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 165397Cupric acetate monohydrateCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

In the above formulae, Bn is a benzyl group. First, copper(II) acetate monohydrate is dissolved in acetic acid, zinc powder is added to this solution, and allyl benzyl ether dissolved in dry diethyl ether was added thereto. Trichloroacetyl chloride and phosphoryl trichloride dissolved in dry diethyl ether are added dropwise to the solution. The reaction solution is refluxed, stirred, returned to room temperature, and filtered. The filtrate is washed, dehydrated, concentrated, and then to the residue are added acetic acid and zinc powder, followed by stirring under reflux. After the reaction solution is filtered, the filtrate is concentrated, the residue is dissolved in ethyl acetate, and zinc powder precipitated upon neutralization is filtered off. This filtrate is separated, washed with saturated NaHCO3 solution and brine, and the organic phase is dehydrated, concentrated, and evaporated under reduced pressure to remove the unreacted allyl benzyl ether, thereby to obtain 3-(benzyloxymethyl)cyclobutanone.

Workup

  1. additionwas added
  2. additionare added dropwise to the solution
  3. temperatureThe reaction solution is refluxed
  4. customreturned to room temperature
  5. filtrationfiltered
  6. washThe filtrate is washed
  7. concentrationconcentrated
  8. additionto the residue are added acetic acid and zinc powder
  9. stirringby stirring
  10. temperatureunder reflux
  11. filtrationAfter the reaction solution is filtered
  12. concentrationthe filtrate is concentrated
  13. dissolutionthe residue is dissolved in ethyl acetate
  14. customzinc powder precipitated upon neutralization
  15. filtrationis filtered off
  16. customThis filtrate is separated
  17. washwashed with saturated NaHCO3 solution and brine
  18. concentrationconcentrated
  19. customevaporated under reduced pressure
  20. customto remove the unreacted allyl benzyl ether

Sources & evidence

ORD record
ord-fe68f9126b3f41b1bf412d7d2bbb5cb2
Source dataset
uspto-grants-2014_12
Patent number
US08907128B2

Reaction notes

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