Dichloroacetyl chloride → HCID 12507350, compound

HRID 1982494Notes

Reaction equation

HRID 1982494 reaction equation
[CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.Cl[CH:8](Cl)[C:9](Cl)=[O:10]>[Zn].C(O)(=O)C>[CH:2]12[CH2:8][C:9](=[O:10])[CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3]2

Participants

5

Reactant 2

HCID 6593Dichloroacetyl chlorideHCID 116051,3-Cyclohexadiene

Product 1

HCID 12507350HCID 12507350, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

The starting material is prepared by the treatment of 1,3-cyclohexadiene with dichloroacetyl chloride, followed by dechlorination with zinc and acetic acid of the resulting adduct to give bicyclo[4,2,0]-oct-2-en-7-one. This compound is subjected to Baeyer-Villiger oxidation to give 7-oxabicyclo[4,3,0]non-2-en-8-one which is treated with thallium (III) nitrate under carefully controlled conditions to give 6-formyl-2-oxabicyclo[3,3,0]octane-3-one having properties identical with those reported by Corey and Ravindranathan, Tetrahedron Letters, 1971, 4753.

Sources & evidence

ORD record
ord-45b7b72e162640208231819c682eee35
Source dataset
uspto-grants-1986_06
Patent number
US04596823

Reaction notes

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