Acetyl chloride → Methyl 4-Formylbenzoate

HRID 1752025Notes

Reaction equation

HRID 1752025 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=[O:2].[C:12](Cl)(=O)C>CO>[CH3:12][O:2][C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 120884-Formylbenzoic acid

Product 1

HCID 15294Methyl 4-FormylbenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Carboxybenzaldehyde (2 mmol) was diluted in 6 mL of anhydrous MeOH. The mixture under N2 was placed in an ice bath and acetyl chloride (10 mmol) was added dropwise. The ice bath was removed and the mixture was stirred overnight at room temperature. The methanol was removed under reduced pressure and the mixture was diluted in 35 mL of EtOAc. The organic phase was washed with 5×10 mL of 1N NaOH and 3×10 mL of brine, dried with MgSO4 and filtered. The volatiles were removed and the product was obtained as a pale yellow solid (96% yield). mp 142-144° C. 1H RMN (CDCl3) δ10.04 (s, 1H), 8.13 (d, 2H, J=8.2 Hz), 7.89 (d, 2H, J=8.1 Hz), 3.90 (s, 3H). 13C NMR (CDCl3) δ 191.91, 166.26, 139.35, 135.27, 130.40, 129.74, 52.81. HRMS (FAB) calcd for C9H9O3 ([M+H]+): 165.0546. found 165.0543.

Workup

  1. customThe mixture under N2 was placed in an ice bath
  2. customThe ice bath was removed
  3. customThe methanol was removed under reduced pressure
  4. additionthe mixture was diluted in 35 mL of EtOAc
  5. washThe organic phase was washed with 5×10 mL of 1N NaOH and 3×10 mL of brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customThe volatiles were removed

Sources & evidence

ORD record
ord-a1931da9a80b446d91d3ba2838ee5cf4
Source dataset
uspto-grants-2015_10
Patent number
US09162991B2

Reaction notes

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