Potassium Carbonate → HCID 12925947、化合物

HRID 894610

反応式

HRID 894610 の反応式
[CH2:1]([O:8][C:9]1[CH:18]=[C:13]([C:14]([O:16]C)=[O:15])[C:12]([OH:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:27]1[CH2:32][CH2:31][O:30][C:28]1=[O:29]>CC(C)=O>[C:14]([C:13]1[CH:18]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=[CH:11][C:12]=1[O:19][CH:27]1[CH2:32][CH2:31][O:30][C:28]1=[O:29])([OH:16])=[O:15]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 13026913Methyl 5-(benzyloxy)-2-hydroxybenzoate

生成物 1

HCID 12925947HCID 12925947、化合物

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a mixture of 32 g of methyl 5-benzyloxysalicylate, 17 g of anhydrous potassium carbonate and 500 ml of acetone was added 30.7 g of α-bromo-γ-butyrolactone under cooling with ice and, then, the mixture was refluxed for 15 hours. After cooling, the acetone was distilled off and 10% methanolic sodium hydroxide was added to the residue for hydrolysis. The reaction mixture was made acidic with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was dissolved in dioxane (300 ml)-benzene (200 ml) and the solution was refluxed in the presence of p-toluenesulfonic acid (30 g), with the resultant water being continuously distilled off. The solvent was distilled off and the residue was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to remove the solvent. The residue was recrystallized from ethyl acetate. By the above procedure there was obtained α-[(2-carboxy-4-benzyloxyphenyl)oxy]-γ-butyrolactone as colorless needles, m.p. 120°-122° C.

後処理

  1. temperatureunder cooling with ice
  2. temperaturethe mixture was refluxed for 15 hours
  3. temperatureAfter cooling
  4. distillationthe acetone was distilled off
  5. addition10% methanolic sodium hydroxide was added to the residue for hydrolysis
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationdistilled
  10. customto remove the solvent
  11. dissolutionThe residue was dissolved in dioxane (300 ml)-benzene (200 ml)
  12. temperaturethe solution was refluxed in the presence of p-toluenesulfonic acid (30 g), with the resultant water being
  13. distillationcontinuously distilled off
  14. distillationThe solvent was distilled off
  15. additionthe residue was diluted with water
  16. extractionextracted with ethyl acetate
  17. washThe extract was washed with water
  18. customdried
  19. concentrationconcentrated
  20. customto remove the solvent
  21. customThe residue was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-5a23af22caa248a99bb08954c267b36c
出典データセット
uspto-grants-1981_08
特許番号
US04284644

関連ノート

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