Ozone → 2-Hydroxy-3-(o-tolylthio)benzaldehyde

HRID 1164106Notes

Reaction equation

HRID 1164106 reaction equation
[O:1]=[O+][O-].[C:4]1([CH3:21])[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=CC)[C:12]=1[OH:20]>C(OCC)(=O)C.C(O)(=O)C>[OH:20][C:12]1[C:11]([S:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH3:21])=[CH:16][CH:15]=[CH:14][C:13]=1[CH:17]=[O:1]

Participants

5

Reactant 2

HCID 24823OzoneHCID 544721892-(o-Tolylthio)-6-(1-propenyl)phenol

Product 1

HCID 130666712-Hydroxy-3-(o-tolylthio)benzaldehyde

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ozone gas was introduced into a solution of 2-(o-tolylthio)-6-(1-propenyl)phenol (24.3 g) in a mixture of ethyl acetate (200 ml) and acetic acid (5 ml) at 3° C. for 1.5 hours. The excess of ozone was removed by air-bubbling and further decomposed with aqueous sodium hydrogen sulfite. The resultant organic layer was separated, washed with aqueous sodium hydrogen sulfite and water in turn, dried and then evaporated under reduced pressure. The oily residue was crystallized with ethanol to give yellow needles of 2-hydroxy-3-(o-tolylthio)benzaldehyde (12.2 g), mp. 42°-43° C.

Workup

  1. customThe excess of ozone was removed
  2. customby air-bubbling
  3. customThe resultant organic layer was separated
  4. washwashed with aqueous sodium hydrogen sulfite and water in turn
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe oily residue was crystallized with ethanol

Sources & evidence

ORD record
ord-6041813b2ee9438fb4c0a85aaaca0a6e
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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