Acetic Acid → HCID 58609527, compound

HRID 502920Notes

Reaction equation

HRID 502920 reaction equation
Cl[C:2]1[CH:3]2[CH2:13][CH2:12][CH:6]([C:7](Cl)(Cl)[C:8]=1[Cl:9])[CH:5]=[CH:4]2.C(O)(=[O:16])C.[OH2:18]>FC(F)(F)C(O)=O.C(OCC)C>[Cl:9][CH:8]1[C:7](=[O:18])[CH:6]2[CH2:12][CH2:13][CH:3]([CH:4]=[CH:5]2)[C:2]1=[O:16]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 68464535HCID 68464535, compound

Product 1

HCID 58609527HCID 58609527, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

0.7 g (2.7 mmol) of 2,3,4,4-tetrachloro-bicyclo[3.2.2]nona-2,6-diene (known from U.S. Pat. No. 3,538,117) is heated in a mixture of 1 ml of trifluoroacetic acid, 4 ml of acetic acid and 1 ml of water for 18 hours at a temperature of 70° C. The cooled reaction solution is then taken up in diethyl ether and extracted first with water and then with saturated sodium chloride solution. After chromatographic purification (ethyl acetate/hexane 1:4), 0.33 g of 3-chloro-bicyclo-[3.2.2]non-6-ene-2,4-dione is obtained as a tautomeric mixture of the forms Da and Db.

Workup

  1. customThe cooled reaction solution
  2. extractionextracted first with water
  3. customAfter chromatographic purification (ethyl acetate/hexane 1:4)

Sources & evidence

ORD record
ord-7e424faabe9f41758dd8a5db1d43c572
Source dataset
uspto-grants-2010_08
Patent number
US07776888B2

Reaction notes

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