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

HRID 1616716

反応式

HRID 1616716 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-50e64329e11f49d6a8ea37592a1fa5f7
出典データセット
uspto-grants-2014_07
特許番号
US08765809B2

関連ノート

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