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

HRID 536209Notes

Reaction equation

HRID 536209 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 (Step 1, 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 brine, dried (MgSO4) and filtered. The solvent was concentrated under reduced pressure to ⅓ volume and the resulting solids were filtered and air-dried to give the title compound (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 brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe solvent was concentrated under reduced pressure
  8. filtrationthe resulting solids were filtered
  9. customair-dried

Sources & evidence

ORD record
ord-5b931fa9ded3445892b568d2e142ba77
Source dataset
uspto-grants-2014_10
Patent number
US08859572B2

Reaction notes

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