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

HRID 42732

Reaction equation

HRID 42732 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

HCID 58325515acrylic acid 4-{2-hydroxy-3-[2-(9-oxo-9H-thioxanthen-2-yloxy)-acetoxy]-propoxy}-butyl esterYield 144.2%

Reagents, catalysts & solvents 3

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 31374DimethylacetamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-0d06cbb7a63845c398af753e17c01870
Source dataset
uspto-grants-2013_09
Patent number
US08536217B2

Linked notes

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