Acetonitrile → acrylic acid 4-{2-hydroxy-3-[2-(9-oxo-9H-thioxanthen-2-yloxy)-acetoxy]-propoxy}-butyl ester

HRID 42732

Reaktionsgleichung

Reaktionsgleichung von HRID 42732
[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[CH:11][C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C(#N)C.[OH:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:33])[CH:31]=[CH2:32].[CH2:34](OCC1OC1)[CH:35]1[O:37][CH2:36]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.CC(N(C)C)=O>[OH:37][CH:35]([CH2:36][O:19][C:18](=[O:20])[CH2:17][O:16][C:13]1[CH:12]=[CH:11][C:10]2[S:9][C:8]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:2](=[O:1])[C:15]=2[CH:14]=1)[CH2:34][O:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:33])[CH:31]=[CH2:32]

Komponenten

7

Edukt 3

HCID 6342AcetonitrileHCID 30198532-(Carboxymethoxy)thioxanthoneHCID 223231504-Hydroxybutylacrylate glycidylether

Produkt 1

HCID 58325515acrylic acid 4-{2-hydroxy-3-[2-(9-oxo-9H-thioxanthen-2-yloxy)-acetoxy]-propoxy}-butyl esterAusbeute 144,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 314042,6-Di-tert-butyl-4-methylphenolKatalysatorHCID 74236Tetrabutylammonium BromideKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A reaction mixture containing (9-oxo-9H-thioxanthen-2-yloxy)acetic acid (4.0 g, 14 mmol), acetonitrile (55 ml), dimethylacetamide (10 mL), tetrabutylammonium bromide (0.5 g, 1.4 mmol) and 2,6-di-tert-butyl-4-methylphenol (0.03 g, 0.114 mmol) was heated to reflux. At this temperature 4-hydroxybutylacrylate glycidylether (2.3 g, 11.4 mmol) was added and the mixture was allowed to stir at reflux temperature for 16 hours. The mixture was cooled to room temperature and the solvent was evaporated under reduced pressure to provide 8.0 g of a yellow oil. The product was purified on a Prochrom LC80 Column using Kromasil Si 60A 10 μm as silica and dichloromethane/ethyl acetate (60/40) as eluent, to afford 1.8 g of a yellow oil.

Aufarbeitung

  1. temperaturewas heated to reflux
  2. temperatureat reflux temperature for 16 hours
  3. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0d06cbb7a63845c398af753e17c01870
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536217B2

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