Hydrochloric Acid → 6-(Acryloyloxy)hexanoic acid

HRID 605445

Reaktionsgleichung

Reaktionsgleichung von HRID 605445
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:10]([C:14]1C=C(C)C=C(C(C)(C)C)[C:15]=1[OH:25])(C)(C)C.C(Cl)(=O)C=C.Cl>O.N1C=CC=CC=1.CC(N(C)C)=O>[C:15]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])(=[O:25])[CH:14]=[CH2:10]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 13140Acryloyl chlorideHCID 144906-Hydroxyhexanoic AcidHCID 314042,6-Di-tert-butyl-4-methylphenol

Produkt 1

HCID 159369966-(Acryloyloxy)hexanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 6-hydroxyhexanoic acid (10 g), 2,6-di-tert-butyl-4-methylphenol (0.5 g), and dimethylacetamide (57 mL) was cooled to 0° C. Acryloyl chloride (17.2 g) was then added dropwise. After stirring for 3.5 hrs, pyridine (12 mL) and water (12 mL) were slowly added. After stirring for another 2 hrs, the solution was acidified with dilute HCl and extracted with ethyl acetate. The combined organic layer was washed with water, dried, filtered, and concentrated to afford 6-acryloyloxyhexanoic acid. 1H NMR (CDCl3, 500 MHz) δ 1.46 (m, 2H), 1.70 (m, 4H), 2.37 (t, J=7.3 Hz, 2H), 4.17 (t, J=6.4 Hz, 2H), 5.82 (d, J=10.4 Hz, 1H), 6.12 (dd, J=17.3, 10.5 Hz, 1H), 6.39 (d, J=17.3 Hz, 1H), 11.59 (br, 1H).

Aufarbeitung

  1. stirringAfter stirring for another 2 hrs
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-10a2bc1a923c4c2cb7ee660e3d52ed8a
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07914700B2

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