Water → 4-(Benzyloxy)-3-nitrobenzaldehyde

HRID 1032511Notes

Reaction equation

HRID 1032511 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C=O>[CH2:19]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 181694-Hydroxy-3-nitrobenzaldehyde

Product 1

HCID 70235544-(Benzyloxy)-3-nitrobenzaldehydeYield 83.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 100° C., 167.0 g of 4-hydroxy-3-nitrobenzaldehyde, 311.0 g of potassium carbonate, and 211.0 g of benzyl chloride are agitated in 2 l of dimethylformamide for 16 hours. The resultant reaction mixture is poured into 10 l of water, the thus-separated solid product is filtered off and recrystallized from ethanol, yielding 215.0 g of 4-benzyloxy-3-nitrobenzaldehyde, mp 100°-102° C.

Workup

  1. customThe resultant reaction mixture
  2. filtrationthe thus-separated solid product is filtered off
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8e320f556b79439184d30adaf4029a84
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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