Potassium Carbonate → Acrylic acid 4-[3-(4-benzoyl-phenoxy)-2-hydroxy-propoxy]butyl ester

HRID 42734

Reaction equation

HRID 42734 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28](=[O:31])[CH:29]=[CH2:30].[CH2:32](OCC1OC1)[CH:33]1[O:35][CH2:34]1>C(#N)C>[C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:32][CH:33]([OH:35])[CH2:34][O:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28](=[O:31])[CH:29]=[CH2:30])=[CH:15][CH:14]=1)(=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143474-HydroxybenzophenoneHCID 223231504-Hydroxybutylacrylate glycidylether

Product 1

HCID 58325536Acrylic acid 4-[3-(4-benzoyl-phenoxy)-2-hydroxy-propoxy]butyl esterYield 101.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture containing 4-hydroxybenzophenone (14.9 g, 75 mmol), acetonitrile (40 mL), potassium carbonate (7.8 g, 56.25 mmol) and 4-hydroxybutylacrylate glycidylether (7.5 g, 37.5 mmol) was heated to reflux. The mixture was allowed to stir at reflux temperature for 24 hours. The mixture was cooled to room temperature and filtered to remove the undissolved potassium carbonate. The filtrate was evaporated under reduced pressure. The residual oil was diluted with ethyl acetate (250 ml) and extracted with a mixture of an aqueous solution of sodium hydroxide (1N) and distilled water (4/1). The organic layer was separated, dried over MgSO4, filtered and evaporated to provide 15.1 g of a yellow oil. The product was purified on a SVP D40 Merck Np Column using dichloromethane/n-hexane (50/50) as eluent, to afford 5.5 g of a yellow oil.

Workup

  1. temperaturewas heated to reflux
  2. temperatureat reflux temperature for 24 hours
  3. filtrationfiltered
  4. customto remove the undissolved potassium carbonate
  5. customThe filtrate was evaporated under reduced pressure
  6. additionThe residual oil was diluted with ethyl acetate (250 ml)
  7. extractionextracted with a mixture of an aqueous solution of sodium hydroxide (1N)
  8. distillationdistilled water (4/1)
  9. customThe organic layer was separated
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-7d59ce6d6e374c768a9c2db1fe3fbb54
Source dataset
uspto-grants-2013_09
Patent number
US08536217B2

Linked notes

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