Triethylamine → p-Ethoxalyloxyethylstyrene

HRID 1197209Notes

Reaction equation

HRID 1197209 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH2:9])=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:19](Cl)([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:20]>C1C=CC=CC=1>[C:19]([O:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH2:9])=[CH:6][CH:5]=1)([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 220518322-(4-Vinylphenyl)ethanol

Product 1

HCID 67847970p-Ethoxalyloxyethylstyrene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
10 °C

Procedure

A 200 ml flask equipped with a stirrer, a thermometer and a dropping funnel was charged with 14.8 g (0.1 mol) of p-hydroxyethylstyrene, 150 ml of benzene and 10.1 g (0.1 mol) of triethylamine and cooled to 10° C. To the mixture was added dropwise with stirring 13.7 g (0.1 mol) of ethoxalyl chloride for one hour at 10° C. to precipitate a hydrochloride of triethylamine (white solid). After mixting at room temperature for 2 hours, 80 g of hexane was added to complete precipitation of the hydrochloride. The hydrochloride is removed by filteration and the resultant filtrate was condensed to obtain the aimed compound. The compound was identified by 1H NMR (360 Mz) and IR. ##STR6##

Workup

  1. customA 200 ml flask equipped with a stirrer
  2. additionTo the mixture was added dropwise
  3. customto precipitate a hydrochloride of triethylamine (white solid)
  4. addition80 g of hexane was added to complete precipitation of the hydrochloride
  5. customThe hydrochloride is removed by filteration
  6. customcondensed

Sources & evidence

ORD record
ord-4d1e49c94e80472fae3f0f3df8388074
Source dataset
uspto-grants-1992_05
Patent number
US05117044

Reaction notes

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