Ethanol → Ethyl Caffeate

HRID 1108181노트

반응식

HRID 1108181 반응식
[C:1]([OH:13])(=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1.S(=O)(=O)(O)O.O.C(=O)(O)[O-].[Na+].[CH2:25](O)[CH3:26]>C(OCC)(=O)C>[C:1]([O:13][CH2:25][CH3:26])(=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1

참가 물질

7

반응물 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 689043Caffeic Acid

생성물 1

HCID 5317238Ethyl Caffeate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Ethyl caffeate was prepared as follows. Caffeic acid (1 g) was boiled under reflux in absolute ethanol (30 ml) in the presence of concentrated sulphuric acid (0.5 ml) for two hours. The reaction mixture was then poured into water (100 ml), and then ethyl acetate (100 ml) and 0.1M sodium bicarbonate solution (100 ml) were added. The organic phase was washed successively with 0.1M sodium bicarbonate solution (3×100 ml) and water (2×100 ml) before being dried (sodium sulphate, anhydrous), filtered and evaporated under vacuum to yield a tan coloured crystalline solid. The product was recrystallised from water giving ethyl caffeate as a tan coloured powder in 43% yield. mp 142-143° C.

후처리

  1. customEthyl caffeate was prepared
  2. washThe organic phase was washed successively with 0.1M sodium bicarbonate solution (3×100 ml) and water (2×100 ml)
  3. dry with materialbefore being dried (sodium sulphate, anhydrous)
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customto yield a tan coloured crystalline solid
  7. customThe product was recrystallised from water

출처 및 근거

ORD 기록
ord-97b3f4f4ae3345a2bd0220757d388c60
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066311

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