Ozone → HCID 20513429, compound

HRID 1163993Notes

Reaction equation

HRID 1163993 reaction equation
[O:1]=[O+][O-].[CH3:4][O:5][C:6]1[C:11]([CH:12]=CC)=[CH:10][CH:9]=[CH:8][C:7]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22]>C(OCC)(=O)C.C(O)(=O)C>[CH3:4][O:5][C:6]1[C:7]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:8][CH:9]=[CH:10][C:11]=1[CH:12]=[O:1]

Participants

5

Reactant 2

HCID 24823OzoneHCID 57276899HCID 57276899, compound

Product 1

HCID 20513429HCID 20513429, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ozone gas was introduced into a solution of 2-chlorophenyl 2-methoxy-3-(1-propenyl)phenyl ether (17.60 g) in a mixture of ethyl acetate (120 ml) and acetic acid (5 ml) at 5° C. for an hour. Thereafter, nitrogen gas was introduced to the reaction mixture to remove the excess of ozone gas, and then dimethyl thioether was added thereto. The mixture was washed with aqueous solution of sodium bicarbonate and water successively, dried over magnesium sulfate and then evaporated. The oily residue was dissolved in diethyl ether, washed with an aqueous solution of sodium bicarbonate, dried and then evaporated to give oily 2-methoxy-3-(2-chlorophenoxy)benzaldehyde (7.0 g).

Workup

  1. additionThereafter, nitrogen gas was introduced to the reaction mixture
  2. customto remove the excess of ozone gas
  3. additiondimethyl thioether was added
  4. washThe mixture was washed with aqueous solution of sodium bicarbonate and water successively
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. dissolutionThe oily residue was dissolved in diethyl ether
  8. washwashed with an aqueous solution of sodium bicarbonate
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-a15fc5518d0047a196dbdc45896970f1
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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