Triphenylphosphine → 4-(3,4-Dichlorobenzyloxy)-3-methylbenzaldehyde

HRID 1515101Notes

Reaction equation

HRID 1515101 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].[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:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:15][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 157283,4-Dichlorobenzyl alcoholHCID 1399014-Hydroxy-3-methylbenzaldehydeHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 230733414-(3,4-Dichlorobenzyloxy)-3-methylbenzaldehydeYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxy-3-methylbenzaldehyde (365 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 purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound was obtained as a white solid (542 mg, yield: 69%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound

Sources & evidence

ORD record
ord-fbada1c884f34569b25d688afebe21b2
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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