Formic Acid → Methyl 5-acetyl-2-chlorobenzoate

HRID 456872Notes

Reaction equation

HRID 456872 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]#[C:11][Si](C)(C)C)[CH:7]=[CH:6][C:5]=1[Cl:16].C(O)=[O:19]>>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10](=[O:19])[CH3:11])[CH:7]=[CH:6][C:5]=1[Cl:16]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 57422929Methyl 2-chloro-5-((trimethylsilyl)ethynyl)benzoate

Product 1

HCID 58818179Methyl 5-acetyl-2-chlorobenzoate

Procedure

A mixture of 2-chloro-5-trimethylsilanylethynyl-benzoic acid methyl ester (3.2 g, 12 mmol) in formic acid (50 mL) was heated at reflux for 16 h. The mixture was cooled to room temperature and concentrated in vacuo. The residue was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was dried, filtered and concentrated in vacuo to afford the title compound (1.4 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with saturated aqueous sodium bicarbonate, water and brine
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29e3c43a88bd4457aa7eeb1e253f5f2b
Source dataset
uspto-grants-2007_03
Patent number
US07186742B2

Reaction notes

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