Epichlorohydrin → 4-phenoxy-O-(2-hydroxy-3-chloropropyl)phenol

HRID 58396

Reaktionsgleichung

[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[O:6]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C>[O:6]([C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:4][CH:3]([OH:5])[CH2:1][Cl:2])=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A four-neck flask equipped with a thermometer, dropping funnel, condenser tube and stirrer was charged with 305.3 g (3.3 mol) of epichlorohydrin, and while nitrogen purging was performed, the temperature was raised to 70° C. Into the flask, 204.8 g (1.1 mol) of 4-phenoxyphenol dissolved in 1020 g of ethanol was added dropwise taking 4 hours. Further, stirring was performed for 6 hours, to complete the addition reaction, for obtaining 4-phenoxy-O-(2-hydroxy-3-chloropropyl)phenol. In succession, the temperature in the flask was lowered to 25° C., and into the flask, 229 g (2.75 mol) of 48% NaOH aqueous solution was added dropwise taking 2 hours. Further, stirring was performed for 1 hour. After completion of cyclization reaction, ethanol was distilled away, and 410 g of toluene was used for extraction, 5% saline solution being used for washing twice. Toluene and epichlorohydrin were removed from the organic layer under reduced pressure, to obtain 215.6 g of a viscous liquid (yield 89%). The purity of 4-phenoxyphenyl glycidyl ether as the main product was 92% (GCarea %).

Aufarbeitung

customA four-neck flask equipped with a thermometer
additionwas added dropwise
waitwas performed for 6 hours
additionthe addition reaction

Quellen und Nachweise

ORD-Eintrag: ord-08902dd1257f4b6f9ee352acd169a027
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09434811B2

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