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

HRID 1464518

반응식

HRID 1464518 반응식
[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]

참가 물질

6

반응물 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 15098222Ethyl 6-(4-methoxyphenyl)-6-oxohexanoateHCID 178418435HCID 178418435, 화합물

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bb3b050121174f6abed579d2c4540a76
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05304658

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