Hydrochloric Acid → 5-Ethoxy-4-hydroxy-2-nitrobenzaldehyde

HRID 1881185Notes

Reaction equation

HRID 1881185 reaction equation
C([O:8][C:9]1[C:16]([O:17][CH2:18][CH3:19])=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([N+:20]([O-:22])=[O:21])[CH:10]=1)C1C=CC=CC=1.Cl>C(O)(=O)C>[CH2:18]([O:17][C:16]1[C:9]([OH:8])=[CH:10][C:11]([N+:20]([O-:22])=[O:21])=[C:12]([CH:15]=1)[CH:13]=[O:14])[CH3:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123199814-(Benzyloxy)-5-ethoxy-2-nitrobenzaldehyde

Product 1

HCID 450942415-Ethoxy-4-hydroxy-2-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Benzyloxy-5-ethoxy-2-nitro-benzaldehyde (23 g) was dissolved in acetic acid (93 ml) and concentrated hydrochloric acid (10 ml). The reaction solution was refluxed for 24 hours. Then the solution was evaporated to dryness and the residue was dissolved in diethyl ether. The product was extracted into 1M sodium hydroxide and acidified with 6M hydrochloric acid. The resultant solid was filtered and dried under vacuum.

Workup

  1. temperatureThe reaction solution was refluxed for 24 hours
  2. customThen the solution was evaporated to dryness
  3. dissolutionthe residue was dissolved in diethyl ether
  4. extractionThe product was extracted into 1M sodium hydroxide
  5. filtrationThe resultant solid was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-a9c9a02e0f0d408dae6ca5b55dcb5a39
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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