Methanol → Methyl 5-Formylsalicylate

HRID 507145Notes

Reaction equation

HRID 507145 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])=[O:2].[CH3:13]O>>[CH3:13][O:9][C:8](=[O:10])[C:7]1[CH:11]=[C:3]([CH:1]=[O:2])[CH:4]=[CH:5][C:6]=1[OH:12]

Participants

3

Reactant 2

HCID 887MethanolHCID 692265-Formylsalicylic acid

Product 1

HCID 14363598Methyl 5-FormylsalicylateYield 79%

Procedure

Heat a mixture of 5-formyl-2-hydroxy-benzoic acid (5.0 g, 30.09 mmol) concentrated sulfuric acid (5 mL) in methanol (100 mL) at reflux for 24 h. Cool the mixture to room temperature and concentrate under reduced pressure. Purify the resulting residue by chromatography over silica gel, eluting with hexanes/ethyl acetate (80:20), to provide the title compound as a colorless oil (4.28 g, 79%). 1H NMR (CDCl3, 300 MHz) δ 3.88 (s, 3H), 4.52 (bs, 1H), 7.05 (d, J=8.56 Hz, 1H), 7.84 (d, J=8.56 Hz, 1H), 8.40 (s, 1H), 9.85 (s, 1H); TLC Rf=0.34 (3:1 Hexanes/Ethyl Acetate).

Workup

  1. temperatureHeat
  2. temperatureat reflux for 24 h
  3. concentrationconcentrate under reduced pressure
  4. customPurify the resulting residue by chromatography over silica gel
  5. washeluting with hexanes/ethyl acetate (80:20)

Sources & evidence

ORD record
ord-f2b4757f34274cfeaf0b48cdbe661e5b
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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