Hydrochloric Acid → 3,4-Dihydroxy-5-nitrobenzaldehyde

HRID 726895Notes

Reaction equation

HRID 726895 reaction equation
C([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[OH:12])[CH:7]=[O:8])C.Cl.C1(C)C=CC=CC=1>O.[Cl-].[Zn+2].[Cl-]>[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[C:11]=1[OH:12])[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 57489573,4-Dihydroxy-5-nitrobenzaldehydeYield 72.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (20.0 g), zinc chloride (60.0 g) and hydrochloric acid (37%, 15 mL) was stirred at 90° C. for 17 h. The mixture was diluted with water (100 mL) and then cooled to 3° C. After 1 h the product was filtered and washed with cold water. The product was dried in vacuo at 100° C. to give 16.5 g (95.1%) of crude product. The crude product was mixed with toluene (275 mL) and activated carbon (2,0 g) and the resulting mixture was refluxed for 45 min. The hot solution was filtered and then cooled to 3° C. After 1 h the product was filtered and washed with cold toluene. It was dried in vacuo at 50° C. to give 12.6 g (72.6%) of pure 3,4-dihydroxy-5-nitrobenzaldehyde (mp. 146°-8° C.).

Workup

  1. temperaturecooled to 3° C
  2. filtrationAfter 1 h the product was filtered
  3. washwashed with cold water
  4. customThe product was dried in vacuo at 100° C.
  5. customto give 16.5 g (95.1%) of crude product
  6. temperaturethe resulting mixture was refluxed for 45 min
  7. filtrationThe hot solution was filtered
  8. temperaturecooled to 3° C
  9. filtrationAfter 1 h the product was filtered
  10. washwashed with cold toluene
  11. customIt was dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-bf99616582274d85b84294cc01faa9d6
Source dataset
uspto-grants-1998_01
Patent number
US05710343

Reaction notes

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