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

HRID 354828Notes

Reaction equation

HRID 354828 reaction equation
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[C:7]([N+:13]([O-:15])=[O:14])[C:6]=1[O:16][CH3:17])(=O)C.[OH-].[Na+].Cl>O>[OH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[C:7]([N+:13]([O-:15])=[O:14])[C:6]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2463194-Formyl-2-methoxy-3-nitrophenyl acetate

Product 1

HCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-Yield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

4-Acetoxy-3-methoxy-2-nitrobenzaldehyde (1120 g., 4.72 moles) was added portionwise to a freshly prepared 33% (w/w) NaOH solution (4.5 liters). The resulting slurry was heated on steam bath at 75° C. for 10 minutes after which it was diluted with 5 liters of water. The reaction mixture was acidified with 6.4 liters of 6 N hydrochloric acid while cooling, and the resulting product (794 g., 85% yield) was filtered and washed with water. Recrystallization from ether/cyclohexane gave the desired product as light yellow solid, M.P. 136°-137° C.

Workup

  1. temperaturewhile cooling
  2. filtrationthe resulting product (794 g., 85% yield) was filtered
  3. washwashed with water
  4. customRecrystallization from ether/cyclohexane

Sources & evidence

ORD record
ord-c16e1bb9b79c420c86b08dcd5ee17867
Source dataset
uspto-grants-1983_03
Patent number
US04377581

Reaction notes

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