Acetonitrile → 3-(4-(Acryloyloxy)butoxy)-2-hydroxypropyl 2-benzoylbenzoate

HRID 42733

Reaction equation

HRID 42733 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#N)C.C([C:25]1C=C(C)C=[C:27](C(C)(C)C)[C:26]=1[OH:36])(C)(C)C.[OH:37][CH2:38][CH2:39][CH2:40][CH2:41][O:42][C:43](=[O:46])[CH:44]=[CH2:45].C(OCC1OC1)C1OC1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(N(C)C)=O>[C:43]([O:42][CH2:41][CH2:40][CH2:39][CH2:38][O:37][CH2:25][CH:26]([OH:36])[CH2:27][O:12][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=1[C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:46])[CH:44]=[CH2:45]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 68132-Benzoylbenzoic AcidHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 223231504-Hydroxybutylacrylate glycidylether

Product 1

HCID 583255113-(4-(Acryloyloxy)butoxy)-2-hydroxypropyl 2-benzoylbenzoate

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 31374DimethylacetamideSolvent

Procedure

A reaction mixture containing 2-benzoyl benzoic acid (40.0 g, 0.1722 mol), acetonitrile (300 mL), dimethylacetamide (10 mL), tetrabutylammonium bromide (5.6 g, 17.22 mmol) and 2,6-di-tert-butyl-4-methylphenol (0.3 g, 1.4 mmol) was heated to reflux. At this temperature 4-hydroxybutylacrylate glycidylether (28.0 g, 140 mmol) was added and the mixture was allowed to stir at reflux temperature for 16 hours.

Workup

  1. temperaturewas heated to reflux
  2. temperatureat reflux temperature for 16 hours

Sources & evidence

ORD record
ord-320c13860a99488e881a36e355cfd6ef
Source dataset
uspto-grants-2013_09
Patent number
US08536217B2

Linked notes

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