Oxygen → Methyl 4-formyl-2-hydroxybenzoate

HRID 1160792Notes

Reaction equation

HRID 1160792 reaction equation
[O:1]=O.[CH3:3][O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=C)=[CH:8][C:7]=1[OH:14].CSC>C(Cl)Cl>[CH3:3][O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:1])=[CH:8][C:7]=1[OH:14]

Participants

5

Reactant 3

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 200893762-Hydroxy-4-vinyl-benzoic acid methyl ester

Product 1

HCID 21626741Methyl 4-formyl-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A steady stream of O2 (g) is passed through a cold (−78° C.) solution of 2-hydroxy-4-vinyl-benzoic acid methyl ester (3.28 g, 0.0184 mol) in CH2Cl2 (50 ml). After 5 minutes, O3 (g) is bubbled into the solution until the solution's color turns blue/gray. The solution is then purged with O2 (g) for 5 minutes, treated with DMS (4.05 ml, 0.0552 mol) and allowed to warm to room temperature overnight. All volatiles are removed in vacuo and the crude product is purified with silica gel column chromatography (0-100% ethyl acetate in hexanes gradient) to afford 4-formyl-2-hydroxy-benzoic acid methyl ester: ESMS m/z 181.0 (M+H+).

Workup

  1. customO3 (g) is bubbled into the solution until the solution's color
  2. customThe solution is then purged with O2 (g) for 5 minutes
  3. customAll volatiles are removed in vacuo
  4. customthe crude product is purified with silica gel column chromatography (0-100% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-50dfd616d60b45768fcd576e814a3371
Source dataset
uspto-grants-2010_10
Patent number
US07816542B2

Reaction notes

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