Benzyl Chloride → HCID 19890468, compound

HRID 620654Notes

Reaction equation

HRID 620654 reaction equation
[CH2:1]([O:5][C:6]1[C:7]([OH:17])=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[C:10]([CH:13]=1)[CH:11]=[O:12])[CH2:2][CH2:3][CH3:4].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:18]([O:17][C:7]1[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:13][C:10]([CH:11]=[O:12])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 19890458HCID 19890458, compound

Product 1

HCID 19890468HCID 19890468, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-butoxy-4-hydroxy-2-nitrobenzaldehyde (31 g; 0.13 mole), benzyl chloride (20.2 g; 0.16 mole) and potassium carbonate (22.11 g; 0.16 mole) in 80 ml of dimethylformamide is heated for 2 hours under reflux with stirring. The reaction mixture is poured into 200 ml of ice-cold water and the precipitate filtered off. After recrystallization in a hexane/toluene mixture, 4-benzyloxy-5-butoxy-2-nitrobenzaldehyde (30.2 g; yield: 71%; yellow powder) is obtained; melting point 94° C.

Workup

  1. temperatureis heated for 2 hours
  2. temperatureunder reflux
  3. filtrationthe precipitate filtered off
  4. customAfter recrystallization in a hexane/toluene mixture

Sources & evidence

ORD record
ord-7b66fe2ccf024a8c8421d9a62ce324c0
Source dataset
uspto-grants-1989_04
Patent number
US04822375

Reaction notes

Loading…