Benzyl Chloride → HCID 19890468, compound

HRID 893549Notes

Reaction equation

HRID 893549 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.CCCCCC.C1(C)C=CC=CC=1>[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

6

Reactant 3

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

Product 1

HCID 19890468HCID 19890468, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21889329Toluene hexaneSolvent

Procedure

One heats for 2 hours under reflux and stirring a mixture of 5-butoxy 4-hydroxy 2-nitro benzaldehyde (31 g, 0.13 mole) of benzyl chloride (20.2 g, 0.18 mole) and of potassium carbonate (22.11 g, 0.16 mole), in 80 ml of dimethylformamide. One pours the reacting mixture in 200 ml ice cold water and filters the precipitate. One obtains after recrystallization in a mixture of hexane-toluene the 4-benzyloxy 5-butoxy 2-nitro benzaldehyde (30.2 g, yield 71%, yellow powder) fusion=94° C.

Workup

  1. temperatureunder reflux
  2. customOne obtains
  3. customafter recrystallization

Sources & evidence

ORD record
ord-3902d8767c2a42f69b90fce2857ba251
Source dataset
uspto-grants-1992_06
Patent number
US05126125

Reaction notes

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