Hydrochloric Acid → 2-HYDROXY-6-NITROBENZALDEHYDE

HRID 1611122Notes

Reaction equation

HRID 1611122 reaction equation
C([O:3][CH:4]1[C:9]2[C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[O:7]CO1)C.Cl>C(O)C.C1COCC1.O1CCOCC1.O>[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:9]=1[CH:4]=[O:3]

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 22258788HCID 22258788, compound

Product 1

HCID 109539092-HYDROXY-6-NITROBENZALDEHYDE

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 4-ethoxy-5-nitro-4H-1,3-benzodioxine (5.80 g, 25.755 mmol) in ethanol (15 mL) and THF (10 mL) was added 4N HCl in 1,4-dioxane (20 mL). The mixture was stirred at 60° C. for 6 hrs and 90° C. for 6 hrs. After cooled to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1) to give 2-hydroxy-6-nitrobenzaldehyde as a pale yellow oil (4.450 g, yield; quant.).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1)
  7. customto give

Sources & evidence

ORD record
ord-d455d5ee5b824c6889ab3b55fe40d720
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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