Sodium Hydroxide → 2-Chloro-3-hydroxy-5-nitro-p-anisaldehyde

HRID 2254756Notes

Reaction equation

HRID 2254756 reaction equation
C([O:4][C:5]1[C:10]([O:11][CH3:12])=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=[C:7]([CH:16]=[O:17])[C:6]=1[Cl:18])(=O)C.[OH-].[Na+]>CO>[Cl:18][C:6]1[C:5]([OH:4])=[C:10]([O:11][CH3:12])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:7]=1[CH:16]=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 144509942-Chloro-3-formyl-6-methoxy-5-nitrophenyl acetate

Product 1

HCID 144509952-Chloro-3-hydroxy-5-nitro-p-anisaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

35.8 g of 2-chloro-3-formyl-6-methoxy-5-nitrophenyl acetate are dissolved in 300 ml of methanol. After adding 145 ml of 1N sodium hydroxide solution the mixture is stirred at 23° for 1 hour. After evaporation of the methanol, the residue is diluted with ice-water, made acid with 2N hydrochloric acid and extracted twice with 400 ml of ethyl acetate each time. The organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated. The residue is recrystallized from methylene chloride/petroleum ether. There is obtained 2-chloro-3-hydroxy-5-nitro-p-anisaldehyde of m.p. 130°.

Workup

  1. customAfter evaporation of the methanol
  2. additionthe residue is diluted with ice-water
  3. extractionextracted twice with 400 ml of ethyl acetate each time
  4. washThe organic phases are washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue is recrystallized from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-43ed4da6ca094758a0bdb52179a8752c
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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