Ozone → HCID 20513447, compound

HRID 1164066Notes

Reaction equation

HRID 1164066 reaction equation
[O:1]=[O+][O-].[CH:4]([C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[CH:10]=[CH:9][C:8]=1[OH:21])=CC>C(O)(=O)C.C(OCC)(=O)C>[OH:21][C:8]1[CH:9]=[CH:10][C:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])=[CH:12][C:7]=1[CH:4]=[O:1]

Participants

5

Reactant 2

HCID 24823OzoneHCID 53759995HCID 53759995, compound

Product 1

HCID 20513447HCID 20513447, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ozone gas was introduced into a solution of 2-(1-propenyl)-4-(2-chlorophenoxy)phenol (14.5 g) in a mixture of acetic acid (10 ml) and ethyl acetate (150 ml) with stirring at 2°-7° C. for an hour. After removing of the excess of ozone gas and addition of aqueous solution of sodium dithionite, the organic layer was separated, washed with saturated aqueous sodium bicarbonate and water, dried and evaporated. The residue was purified by column chromatography (silical gel, benzene) to give oily 2-hydroxy-5-(2-chlorophenoxy)benzaldehyde (10.4 g).

Workup

  1. customAfter removing of the
  2. additionexcess of ozone gas and addition of aqueous solution of sodium dithionite
  3. customthe organic layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate and water
  5. customdried
  6. customevaporated
  7. customThe residue was purified by column chromatography (silical gel, benzene)

Sources & evidence

ORD record
ord-a35fd9633b554a298666f2be2995bf18
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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