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

HRID 41111

反応式

HRID 41111 の反応式
[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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 143474-HydroxybenzophenoneHCID 223231504-Hydroxybutylacrylate glycidylether

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A reaction mixture containing 4-hydroxybenzophenone (14.9 g, 75 mmol), acetonitrile (40 mL), potassium carbonate (7.8 g, 56.3 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.

後処理

  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

出典と根拠

ORDレコード
ord-afef5ba57e84498ea85c596ad7f908ff
出典データセット
uspto-grants-2013_09
特許番号
US08530510B2

関連ノート

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