2,4-dimethoxy-5-nitrobenzaldehyde → 2,4-Dihydroxy-5-nitrobenzaldehyde

HRID 1751844Notes

Reaction equation

HRID 1751844 reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([O:11]C)[C:8]([N+:13]([O-:15])=[O:14])=[CH:7][C:4]=1[CH:5]=[O:6].C[S-].[Na+]>CN(C)C(=O)C.O>[OH:2][C:3]1[CH:10]=[C:9]([OH:11])[C:8]([N+:13]([O-:15])=[O:14])=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

5

Reactant 2

HCID 2312412,4-dimethoxy-5-nitrobenzaldehydeHCID 4378561Sodium methanethiolate

Product 1

HCID 7354562,4-Dihydroxy-5-nitrobenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

2,4-dimethoxy-5-nitro-benzaldehyde (135 mg, 0.638 mmol) and sodium methanethiolate (125 mg, 1.78 mmol) are dissolved in 4 ml of N,N-dimethylacetamide and heated at 80° C. for 26 h. The reaction mixture is diluted to 50 ml with water and extracted with dichloromethane. The aqueous layer is then acidified with 5% HCl and extracted again with dichloromethane. All of the organic layers are dried over Na2SO4, concentrated, and purified using silica gel chromatography (100% dichloromethane to 30% acetone in dichloromethane) to yield 2,4-dihydroxy-5-nitro-benzaldehyde.

Workup

  1. extractionextracted with dichloromethane
  2. extractionextracted again with dichloromethane
  3. dry with materialAll of the organic layers are dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-cbe4bca1ca7244f2bbc47529155fa352
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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