Hydrochloric Acid → 2-Allyl-2,3,3-trichlorocyclohexanone

HRID 399341Notes

Reaction equation

HRID 399341 reaction equation
[CH2:1]([CH:4]1[C:10]([Cl:12])([Cl:11])[CH2:9][CH2:8][CH:7]2[C:5]1(Cl)[O:6]2)[CH:2]=[CH2:3].N1C=CC=CC=1.[ClH:20]>>[CH2:1]([C:4]1([Cl:20])[C:10]([Cl:12])([Cl:11])[CH2:9][CH2:8][CH2:7][C:5]1=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 189709622-Allyl-1,3,3-trichloro-7-oxabicyclo[4.1.0]heptane

Product 1

HCID 189709642-Allyl-2,3,3-trichlorocyclohexanone

Procedure

1.60 g (6.62 mmol) of epoxide 2j and 2 cm3 (25 mmol) of pyridine were heated to reflux for 24 h. After cooling, the mixture was acidified to pH=1 with 3N HCl, extracted with ether (3×30 cm3), dried over MgSO4 filtered and evaporated down. The crude product was purified by flash chromatography on silica (eluent: ether/petroleum ether=1/99). The following were isolated (in the order of elution): starting epoxide 2j, 0.40 g of transposition ketone 6a (Yld=40%), traces of 2-allyl-2,3-dichloro-3-cyclohexenone 7 (evidence based on GC/mass) and phenol 4f.

Workup

  1. temperatureto reflux for 24 h
  2. temperatureAfter cooling
  3. extractionextracted with ether (3×30 cm3)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated down
  7. customThe crude product was purified by flash chromatography on silica (eluent: ether/petroleum ether=1/99)
  8. customThe following were isolated (
  9. washin the order of elution):

Sources & evidence

ORD record
ord-d1279236ebae48619b3686c0c258c70e
Source dataset
uspto-grants-1998_10
Patent number
US05817890

Reaction notes

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