Nitric Acid → 3-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

HRID 726894Notes

Reaction equation

HRID 726894 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[OH:16])[CH:11]=[O:12])[CH3:6]>ClCCl>[CH2:5]([O:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([N+:1]([O-:4])=[O:2])[C:15]=1[OH:16])[CH:11]=[O:12])[CH3:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 8467Ethylvanillin

Product 1

HCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
3 °C

Procedure

Fuming nitric acid (22.0 mL) was added (rate approx. 1.5 mL/min) to a stirred solution of 3-ethoxy-4-hydroxybenzaldehyde (83.0 g) in dichloromethane (400 mL) at 5°-10° C. Thereafter the mixture was stirred for 30 min at 3° C. and then filtered. The product was washed with dichloromethane and water and dried in vacuo at 50° C., yield 77.8 g (73,7%).

Workup

  1. filtrationfiltered
  2. washThe product was washed with dichloromethane and water
  3. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-bb4dd3b4437645d2b68d32ae6430f5a3
Source dataset
uspto-grants-1998_01
Patent number
US05710343

Reaction notes

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