Triphenylphosphine → 4-[(3,4-Dichlorophenyl)methoxy]-3-nitrobenzaldehyde

HRID 1515102Notes

Reaction equation

HRID 1515102 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].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:17]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:17][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]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 157283,4-Dichlorobenzyl alcoholHCID 181694-Hydroxy-3-nitrobenzaldehydeHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 45918044-[(3,4-Dichlorophenyl)methoxy]-3-nitrobenzaldehydeYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxy-3-nitrobenzaldehyde (448 mg, 2.68 mmol), 3,4-dichlorobenzyl alcohol (665 mg, 3.76 mmol), and triphenylphosphine (980 mg, 3.74 mmol) were dissolved in tetrahydrofuran (8 mL), and a diethyl azodicarboxylate toluene solution (2.2 M, 1.71 mL, 3.76 mmol) was slowly added dropwise thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. The solvent was distilled off under reduced pressure, and the resulting residue was washed with hexane/dichloromethane (6/1 (v/v)), whereby the objective title compound was obtained as a yellow solid (351 mg, yield: 40%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. washthe resulting residue was washed with hexane/dichloromethane (6/1 (v/v)), whereby the objective title compound

Sources & evidence

ORD record
ord-b2b561c1997c4144bcc4bb3563cdf97a
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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