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

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

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.