Dihydroferulic Acid → 8-Methylnonyl 3-(4-hydroxy-3-methoxyphenyl)propionate

HRID 1510992

반응식

HRID 1510992 반응식
[CH3:1][CH:2]([CH3:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21](O)=[O:22])=[CH:15][C:14]=1[O:24][CH3:25].S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1>[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]([CH3:11])[CH3:1])=[O:22])=[CH:15][C:14]=1[O:24][CH3:25]

참가 물질

5

반응물 3

HCID 14340Dihydroferulic AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 32898Isodecanol

생성물 1

HCID 689859808-Methylnonyl 3-(4-hydroxy-3-methoxyphenyl)propionate수율 76.5%

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
50 °C

실험 절차

8-Methyl-1-nonanol (752 mg, 4.74 mmol), 3-(4-hydroxy-3-methoxyphenyl)propionic acid (977 mg, 4.98 mmol) and Novozyme 435 (100 mg) were measured and placed in a flask (25 ml). Toluene (5 ml) and anhydrous magnesium sulfate (1 g) were added, and the mixture was stirred with heating in an oil bath at 50° C. for 16 hr. The reaction mixture was allowed to cool to room temperature, toluene (25 ml) was added, and Novozyme 435 and the precipitated insoluble material were removed by filtration. Toluene (50 ml) was added, and the mixture was washed with 5% aqueous sodium hydrogen carbonate solution (25 ml×3) and saturated brine (25 ml) and dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was developed by PTLC (chloroform:n-hexane:ethyl acetate=1:1:1), and silica gel containing the object product was stirred with ethyl acetate (100 ml) for 30 min for extraction. The silica gel was filtered off, and the filtrate was concentrated under reduced pressure to give 8-methylnonyl 3-(4-hydroxy-3-methoxyphenyl)propionate (1.22 g, yield 76.2%) as a colorless oil.

후처리

  1. customplaced in a flask
  2. temperatureto cool to room temperature
  3. customNovozyme 435 and the precipitated insoluble material were removed by filtration
  4. additionToluene (50 ml) was added
  5. washthe mixture was washed with 5% aqueous sodium hydrogen carbonate solution (25 ml×3) and saturated brine (25 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationMagnesium sulfate was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. stirringwas stirred with ethyl acetate (100 ml) for 30 min for extraction
  10. filtrationThe silica gel was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-48579746086745308893e4536072f80b
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08212068B2

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