Triphenylphosphine → HCID 19088824, compound

HRID 257527Notes

Reaction equation

HRID 257527 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH2:11][CH3:12])[CH3:10])[CH:5]=[CH:4][C:3]=1[OH:13].[CH2:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]O)=[CH:18][CH:17]=1)[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:9]([O:8][C:6]1[CH:5]=[CH:4][C:3]([O:13][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([CH2:14][CH3:15])=[CH:17][CH:18]=2)=[C:2]([Cl:1])[CH:7]=1)([CH2:11][CH3:12])[CH3:10]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 130344-Ethylbenzyl alcoholHCID 229187772-Chloro-4-sec-butoxyphenol

Product 1

HCID 19088824HCID 19088824, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.74 g of 2-chloro-4-sec-butoxyphenol, 0.50 g of p-ethylbenzyl alcohol, 1.00 g of triphenylphosphine, 0.65 g of diethylazadicarboxylate 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 0.71 g of 1-sec-butoxy-3-chloro-4-(4-ethylbenzyloxy)-benzene. Yield, 60%. nD22.6 1.5529.

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-4478fc9b401b47ab87c48833dcdcc443
Source dataset
uspto-grants-1993_11
Patent number
US05262441

Reaction notes

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