Hydrochloric Acid → Methyl 4-Formylbenzoate

HRID 1274220Notes

Reaction equation

HRID 1274220 reaction equation
Cl.[C:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)([OH:4])=[O:3].[CH3:13]O>>[CH3:13][O:3][C:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 120884-Formylbenzoic acid

Product 1

HCID 15294Methyl 4-FormylbenzoateYield 100%

Procedure

Methanol (50 ml) was cooled (0°) and saturated with hydrogen chloride gas. p-Carboxybenzaldehyde (5.0 g) was added and the resulting solution stirred at room temperature for 3 days. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and 5M hydrochloric acid. The organic layer was washed twice with water and dried. The solvent was removed to afford the product as a white solid (5.40 g, 100%). δH (CDCl3) 3.96 (3H, s), 7.96 (2H, dd, J 6.8 and 1.7 Hz), 8.20 (2H, dd, J 6.8 and 1.7 Hz), 10.11 (1H, s) ppm.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and 5M hydrochloric acid
  3. washThe organic layer was washed twice with water
  4. customdried
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-670f93dcb4f04be6abb205438a2d822c
Source dataset
uspto-grants-2000_12
Patent number
US06156774

Reaction notes

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