Formic Acid → Methyl 4-acetyl-3-hydroxybenzoate

HRID 2306659Notes

Reaction equation

HRID 2306659 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[C:13][Si](C)(C)C)[C:5]([O:7][CH3:8])=[O:6].C(O)=[O:19]>>[C:12]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[OH:1])(=[O:19])[CH3:13]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 22481756Methyl 3-hydroxy-4-[2-(trimethylsilyl)ethynyl]benzoate

Product 1

HCID 22610067Methyl 4-acetyl-3-hydroxybenzoateYield 83%

Conditions

Temperature
80 °C

Procedure

Methyl 3-hydroxy-4-[(trimethylsilyl)ethynyl]benzoate (540 mg, 2.17 mmole) is combined with 4 ml formic acid under nitrogen. The reaction is warmed to 80° C. for 12 h, is cooled to rt, and the volatiles are removed in vacuo. The black residue is chromatographed over 25 g silica gel (230-400 mesh) eluting with 15% EtOAc/hexane. The appropriate fractions are combined and concentrated to provide 350 mg (83%) of methyl 4-acetyl-3-hydroxybenzoate as a pale yellow solid. 1H NMR (CDCl3) δ 2.70, 3.95, 7.54, 7.64, 7.82, 12.10 ppm.

Workup

  1. temperatureis cooled to rt
  2. customthe volatiles are removed in vacuo
  3. customThe black residue is chromatographed over 25 g silica gel (230-400 mesh)
  4. washeluting with 15% EtOAc/hexane
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe0cfcda2c6243e1a04b5eab288ff73b
Source dataset
uspto-grants-2004_12
Patent number
US06828330B2

Reaction notes

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