Ethanol → Ethyl Caffeate

HRID 1108181Notes

Reaction equation

HRID 1108181 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

HCID 5317238Ethyl Caffeate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-97b3f4f4ae3345a2bd0220757d388c60
Source dataset
uspto-grants-2000_05
Patent number
US06066311

Reaction notes

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