Hydrochloric Acid → 6-Ethoxy-6-(4-methoxyphenyl)hexanoic acid

HRID 1646814

反応式

HRID 1646814 の反応式
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])=[O:8])=[CH:5][CH:4]=1.B.[Na].O.Cl.[CH2:24](O)[CH3:25]>>[CH2:24]([O:8][CH:7]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=1)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH3:25]

参加物

6

反応物 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 15098222Ethyl 6-(4-methoxyphenyl)-6-oxohexanoateHCID 178418435HCID 178418435、化合物

生成物 1

HCID 190880606-Ethoxy-6-(4-methoxyphenyl)hexanoic acid

実験手順

A solution of ethyl 5-(4-methoxybenzoyl)pentanoate (50 g, 0.19 mole) in ethanol (500 ml) was cooled with ice, and sodium boron hydride (10 g) was added gradually to the solution. After the reaction was allowed to proceed for 1 hour, water (200 ml) and 2N hydrochloric acid (50 ml) were added to the reaction solution, followed by concentration under reduced pressure. The resulting residue was dissolved in ethyl acetate, and the organic layer was washed with water, dried and concentrated under reduced pressure. Methanol (300 ml), water (100 ml) and sodium hydroxide (40 g) were added to the resulting residue, followed by stirring for 2 hours, and the methanol was removed under reduced pressure. The water layer was washed with isopropyl ether and then adjusted to pH 4.0 with hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure, and the residue was chromatographed on a silica gel column, followed by elution with isopropyl ether-ethyl acetate (1:1) to give firstly 6-ethoxy-6-(4-methoxyphenyl)hexanoic acid (21 g) and then 6-hydroxy-6-(4-methoxyphenyl)hexanoic acid (20 g).

後処理

  1. additionwas added gradually to the solution
  2. concentrationfollowed by concentration under reduced pressure
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washthe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. additionMethanol (300 ml), water (100 ml) and sodium hydroxide (40 g) were added to the resulting residue
  8. customthe methanol was removed under reduced pressure
  9. washThe water layer was washed with isopropyl ether
  10. extractionfollowed by extraction with ethyl acetate
  11. washThe organic layer was washed with water
  12. customdried
  13. concentrationconcentrated under reduced pressure
  14. customthe residue was chromatographed on a silica gel column
  15. washfollowed by elution with isopropyl ether-ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-79e909781afb407f85d2a8d64201e80c
出典データセット
uspto-grants-1993_01
特許番号
US05180742

関連ノート

読み込み中…