Triphenylphosphine → HCID 19088824, compound

HRID 1463915Notes

Reaction equation

HRID 1463915 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-fde39e4cdc734369acca70ca14c43bb8
Source dataset
uspto-grants-1994_04
Patent number
US05302619

Reaction notes

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