2,4-Dinitrotoluene → 4'-Benzyloxy-2,4-dinitrostilbene

HRID 900637

Reaction equation

HRID 900637 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH3:13])([O-:3])=[O:2].[CH2:14]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1CCCC1>CN(C)C=O.C(O)(C)C>[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][C:25](/[CH:26]=[CH:13]/[C:5]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:28][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 84612,4-DinitrotolueneHCID 31268PyrrolidineHCID 78109Benzaldehyde, 4-(phenylmethoxy)-

Product 1

HCID 62665174'-Benzyloxy-2,4-dinitrostilbene

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

18.21 g (0.1 mol) of 2,4-dinitrotoluene, 21.23 g (0.1 mol) of 4-benzyloxy-benzaldehyde and 1.8 mL of pyrrolidine in 140 mL of dimethylformamide were heated for 2 hours at 100° C. which caused the reaction mixture to assume a dark-brown color. The reaction mixture was then allowed to cool to room temperature after which it was diluted with 210 mL of isopropanol and allowed to agitate for an additional hour with ice cooling. The product was suction-filtered off, washed with a small amount of cold isopropanol and then dried at 40° C. under vacuum.

Workup

  1. filtrationThe product was suction-filtered off
  2. washwashed with a small amount of cold isopropanol
  3. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-74d8dca085304fa79d194630aa2f71d8
Source dataset
uspto-grants-2008_04
Patent number
US07361198B2

Linked notes

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