Hydrochloric Acid → Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-

HRID 339759Notes

Reaction equation

HRID 339759 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[C:7]([N+:13]([O-:15])=[O:14])[C:6]=1[O:16][CH3:17])(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO.O>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[C:7]([N+:13]([O-:15])=[O:14])[C:6]=1[O:16][CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2463194-Formyl-2-methoxy-3-nitrophenyl acetate

Product 1

HCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-Yield 89.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-formyl-2-methoxy-3-nitrophenyl acetate 438 g (1.8 mol) and potassium carbonate (506 g, 3.7 mol) in MeOH (4000 mL) was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure to afford a viscous oil. This was dissolved in water, acidified using a solution of HCl (2 N) and extracted with EtOAc. The organic layer was washed with a saturated sodium chloride solution, dried (magnesium sulfate) and filtered. The solvent was concentrated under reduced pressure to ⅓ volume and the resulting solids were filtered and air-dried to give 4-hydroxy-3-methoxy-2-nitrobenzaldehyde (317 g, 88%): 1H NMR (DMSO-d6) δ: 9.69 (1H, s), 7.68 (1H, d), 7.19 (1H, d), 3.82 (3H, s).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford a viscous oil
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationThe solvent was concentrated under reduced pressure
  8. filtrationthe resulting solids were filtered
  9. customair-dried

Sources & evidence

ORD record
ord-cb349b84579d4426b07c278e49cff373
Source dataset
uspto-grants-2014_11
Patent number
US08895549B2

Reaction notes

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