Sodium Chloride → 3,4-Dihydroxystyrene

HRID 1110093Notes

Reaction equation

HRID 1110093 reaction equation
C(O)(=O)/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1.[Cl-].[Na+]>CN(C)C=O>[OH:7][C:6]1[CH:5]=[C:4]([CH:11]=[CH:10][C:8]=1[OH:9])[CH:3]=[CH2:2]

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 689043Caffeic Acid

Product 1

HCID 1513983,4-Dihydroxystyrene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

200 g (1.11 mol) of caffeic acid are dissolved in 1.2 l of dimethyl formamide dissolved and the solution is stirred for 3 h at 150° C. After cooling to room temperature, the solution is poured on to 3 kg of ice, saturated with sodium chloride and extracted twice with ethyl acetate. The organic phase is washed with 2% NaHCO3 solution and then with water, dried over Na2SO4 and concentrated by evaporation, giving 120 g (80% ) of a highly viscous liquid which can be recrystallised from toluene. The substance is, however, sufficiently pure and can be further processed without recrystallisation.

Workup

  1. dissolutiondissolved
  2. temperatureAfter cooling to room temperature
  3. extractionextracted twice with ethyl acetate
  4. washThe organic phase is washed with 2% NaHCO3 solution
  5. dry with materialwith water, dried over Na2SO4
  6. concentrationconcentrated by evaporation
  7. customgiving 120 g (80% ) of a highly viscous liquid which
  8. customcan be recrystallised from toluene
  9. customhowever, sufficiently pure and can be further processed without recrystallisation

Sources & evidence

ORD record
ord-b98248f5fe4644aea912c67d1f7d262a
Source dataset
uspto-grants-1994_06
Patent number
US05324804

Reaction notes

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