Triphenylphosphine → HCID 19088821, compound

HRID 1463914Notes

Reaction equation

HRID 1463914 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[OH:14].[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]O)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[O:14][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([Cl:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 133974-Chlorobenzyl alcoholHCID 19088818HCID 19088818, compound

Product 1

HCID 19088821HCID 19088821, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.75 g of 2-chloro-4-(2-ethylbutyl)phenol, 0.50 g of p-chlorobenzyl alcohol, 0.92 g of triphenylphosphine, 0.71 g of diisopropylazadicarboxylate and 100 mg of tetrahydrofuran was stirred at room temperatur for 48 hours. The reaction mixture was concentrated, and 50 ml of diethyl ether was added thereto. The precipitates were removed by filtration, and the filtrate was concentrated. The residue was subjected to silica gel chromatography to give 0.75 g of 2-chloro-1-(4-chlorobenzyloxy)-4-(2-ethylbutyl)benzene. Yield, 63%. nD22.6 1.5611.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition50 ml of diethyl ether was added
  3. customThe precipitates were removed by filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7d96939b8a2d439199b04c380b920100
Source dataset
uspto-grants-1994_04
Patent number
US05302619

Reaction notes

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