Ethanol → HCID 18979200、化合物

HRID 2393178ノート

反応式

HRID 2393178 の反応式
[N+:1]([O-:4])(O)=[O:2].[CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=[O:22].C(O)C.[OH-].[Na+]>C(OC(=O)C)(=O)C>[N+:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])([O-:4])=[O:2]

参加物

6

反応物 4

HCID 702EthanolHCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 18979239HCID 18979239、化合物

生成物 1

HCID 18979200HCID 18979200、化合物

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒2 回

反応条件

温度
-78 °C

実験手順

Fuming nitric acid (81 ml) was ice-cooled and acetic anhydride (4.5 ml) was added dropwise. The mixture was cooled to -78° C. and a solution of ethyl 7-(2-naphthyl)heptanoate (10 g) in acetic anhydride (20 ml) was added. The temperature was then increased to -20° C. over a period of 2 hours, after which ethanol (10 ml) was added dropwise. The mixture was stirred for 30 minutes. Then, 2N aqueous sodium hydroxide solution (300 ml) was added under ice-cooling and the mixture was further stirred for 2 hours and, then, extracted with ether. The organic layer was washed with water, dried, and concentrated to dryness. The solid residue (11 g) was added to 5N aqueous sodium hydroxide solution (66 ml)-tetrahydrofuran (264 ml) and the mixture was refluxed for 6 hours. The reaction mixture was acidified with HCl and extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated to dryness and the residue was recrystallized from hexane-ethyl acetate to provide 7-(1-nitro-2-naphthyl)heptanoic acid (3.4 g).

後処理

  1. temperaturecooled
  2. temperatureThe temperature was then increased to -20° C. over a period of 2 hours
  3. temperaturecooling
  4. stirringthe mixture was further stirred for 2 hours
  5. extractionextracted with ether
  6. washThe organic layer was washed with water
  7. customdried
  8. concentrationconcentrated to dryness
  9. additionThe solid residue (11 g) was added to 5N aqueous sodium hydroxide solution (66 ml)-tetrahydrofuran (264 ml)
  10. temperaturethe mixture was refluxed for 6 hours
  11. extractionextracted with ethyl acetate
  12. washThe organic layer was washed with water
  13. customdried
  14. concentrationconcentrated to dryness
  15. customthe residue was recrystallized from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-db537bb4cbda4becb141df3ce2bb764b
出典データセット
uspto-grants-1998_09
特許番号
US05804601

反応ノート

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