Chloroacetyl chloride → 4-Chloroacetoxystyrene

HRID 78872

Reaktionsgleichung

Reaktionsgleichung von HRID 78872
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[Cl:10][CH2:11][C:12](Cl)=[O:13].CCN(CC)CC>C(OCC)C>[Cl:10][CH2:11][C:12]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1)=[O:13]

Komponenten

5

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 624534-Vinylphenol

Produkt 1

HCID 593017254-ChloroacetoxystyreneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxystyrene (1.22 g, 10 mmol) in ethyl ether 140 mL was added chloroacetic chloride (2.26 g, 20 mmol) and Et3N (1.62 g, 16 mmol). After it was stirred for 2 h, the mixture was washed with brine and water. The ether solution was dried over Na2SO4 and concentrated. After purification by flash column, the 4-chloroacetoxystyrene (1.8 g, 92%) was obtained. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.46 (d, 2H, J=1.8 Hz), 7.11 (d, 2H, J=8.4 Hz), 6.73 (dd, 1H, J=17.7 Hz), 5.74 (d, 1H, J=18 Hz), 5.29 (d, J=11.1 Hz), 4.31 (s, 2H). 13C NMR (CDCl3, 75 MHz) δ166.0, 150.0, 136.0, 135.8, 127.4, 121.3, 114.6, 41.0.

Aufarbeitung

  1. washthe mixture was washed with brine and water
  2. dry with materialThe ether solution was dried over Na2SO4
  3. concentrationconcentrated
  4. customAfter purification by flash column

Quellen und Nachweise

ORD-Eintrag
ord-ce85750783754e19ad06d30209c70b4a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841477B2

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