Hydrochloric Acid → 1-(3,4-Dimethoxyphenyl)-4,4-dimethyl-1,3-pentanedione

HRID 1885763ノート

反応式

HRID 1885763 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:8]([O:10]C)=O.[CH3:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].Cl>CCCCCC.O1CCCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:8](=[O:10])[CH2:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 16522Methyl 3,4-DimethoxybenzoateHCID 24758Sodium hydride

生成物 1

HCID 113345631-(3,4-Dimethoxyphenyl)-4,4-dimethyl-1,3-pentanedione収率 66%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

In a 200 ml three-necked flask equipped with a mechanical stirrer, dropping funnel, reflux condenser, and a nitogen-inlet tube, 2.45 gm (61 mmol) of 60% sodium hydride, 10 gm (51 mmol) of methyl 3,4-dimethoxybenzoate, and 100 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream, and refluxed with heating while 6.1 gm (61 mmol) of pinacolone was added dropwise. The refluxing under heat was continued for 7 hours. After cooling the reaction mixture, 30 ml of 2N hydrochloric acid was added and the mixture was extracted twice with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was removed by evaporation to give a crude product. Hexane was added to the crude product and insoluble substances were filtered off. The filtrate was concentrated by evaporation, and recrystallization afforded 8.9 gm of the target compound as colorless needles (yield: 65%).

後処理

  1. customIn a 200 ml three-necked flask equipped with a mechanical stirrer
  2. temperaturereflux condenser, and a nitogen-inlet tube
  3. temperaturerefluxed
  4. additionwas added dropwise
  5. temperatureThe refluxing under heat
  6. additionwas added
  7. extractionthe mixture was extracted twice with chloroform
  8. dry with materialThe extract was dried over anhydrous sodium sulfate
  9. customthe solvent was removed by evaporation
  10. customto give a crude product
  11. filtrationwere filtered off
  12. concentrationThe filtrate was concentrated by evaporation, and recrystallization

出典と根拠

ORDレコード
ord-6d003e1a56ad452f974a0415907a01ca
出典データセット
uspto-grants-1992_09
特許番号
US05146002

反応ノート

読み込み中…