Triphenylphosphine → HCID 77231378, compound

HRID 1515103Notes

Reaction equation

HRID 1515103 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:15]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:1][C:2]1[CH:9]=[C:8]([O:10][CH2:15][C:14]2[CH:17]=[CH:18][C:19]([Cl:20])=[C:12]([Cl:11])[CH:13]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 157283,4-Dichlorobenzyl alcoholHCID 1853632-Chloro-4-hydroxybenzaldehydeHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 77231378HCID 77231378, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-4-hydroxybenzaldehyde (324 mg, 2.07 mmol), 3,4-dichlorobenzyl alcohol (513 mg, 2.90 mmol), and triphenylphosphine (760 mg, 2.90 mmol) were dissolved in tetrahydrofuran (8 mL), and a diethyl azodicarboxylate toluene solution (2.2 M, 1.32 mL, 2.90 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 in the reaction solution 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 white solid (244 mg, yield: 37%).

Workup

  1. distillationThe solvent in the reaction solution 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-94cc8566614445aba7fc4e3d1ecba1e6
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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