Sodium Bicarbonate → 4-Chloro-2-formylbenzoic acid

HRID 655829Notes

Reaction equation

HRID 655829 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:4]=1[C:5](NC)=[O:6])=[O:2].C(=O)([O-])[OH:15].[Na+]>Cl>[CH:1]([C:3]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:4]=1[C:5]([OH:15])=[O:6])=[O:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 577253672-formyl-4-chloro-N-methylbenzamide

Product 1

HCID 110414214-Chloro-2-formylbenzoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 2-formyl-4-chloro-N-methylbenzamide (3.19 g) and 10M hydrochloric acid (30 ml) was heated at reflux for 18 hours. The mixture was cooled and basified with saturated sodium hydrogen carbonate solution. The solution was then washed with ethyl acetate, then acidified with 2M hydrochloric acid. The product was extracted with ethyl acetate and the combined extracts dried with magnesium sulfate. The solution was then filtered and concentrated. This furnished 2-formyl-4-chlorobenzoic acid as a yellow solid (2.22 g, 75%); 1H NMR (400 MHz, CDCl3) δ 6.65 (0.5H, brs), 7.50 (2H, m), 7.65 (1H, m), 7.85 (0.5H, brm), 8.05 (1H, m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. washThe solution was then washed with ethyl acetate
  5. extractionThe product was extracted with ethyl acetate
  6. dry with materialthe combined extracts dried with magnesium sulfate
  7. filtrationThe solution was then filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-47d04d663d25480da1531e63c71b2b25
Source dataset
uspto-grants-2011_12
Patent number
US08071618B2

Reaction notes

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