Ozone → 2-Hydroxy-3-(2-chlorophenylthio)benzaldehyde

HRID 1164077Notes

Reaction equation

HRID 1164077 reaction equation
[O:1]=[O+][O-].[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=CC)[C:13]=1[OH:21]>C(OCC)(=O)C.C(O)(=O)C>[OH:21][C:13]1[C:12]([S:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[Cl:4])=[CH:17][CH:16]=[CH:15][C:14]=1[CH:18]=[O:1]

Participants

5

Reactant 2

HCID 24823OzoneHCID 540729152-(2-Chlorophenylthio)-6-(1-propenyl)phenol

Product 1

HCID 205134432-Hydroxy-3-(2-chlorophenylthio)benzaldehyde

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ozone gas was introduced into a solution of 2-(2-chlorophenylthio)-6-(1-propenyl)phenol (26 g) in a mixture of ethyl acetate (200 ml) and acetic acid (10 ml) at temperature below 0° C. with stirring for an hour. The precipitates were collected by filtration, washed with ethyl acetate and then dried to give 2-hydroxy-3-(2-chlorophenylthio)benzaldehyde (15.9 g), mp. 111°-112.5° C. The filtrate and washings were combined, washed with dil. aqueous sodium hydrogen sulfite, saturated aqueous sodium bicarbonate and water in turn, dried over magnesium sulfate and then evaporated under reduced pressure. The residue was washed with methanol and dried to give the same product (3.2 g). Total yield 19.1 g.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-2155e89ccf3d4bd098ed24ceae3c55a4
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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