Hydrochloric Acid → 4-Methoxy cinnamic acid

HRID 2210289Notes

Reaction equation

HRID 2210289 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].C(NCC)C.Cl>[Pd].CN(C)C=O.C(OCC)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:12]=[CH:11][C:10]([OH:14])=[O:13])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6581Acrylic AcidHCID 8021DiethylamineHCID 696764-Iodoanisole

Product 1

HCID 132454-Methoxy cinnamic acidYield 65%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2.34 g (10 mmol) of p-iodoanisole, 0.756 g (10.5 mmol) of acrylic acid, 0.803 g (11 mmol) of diethylamine and 16 mg of palladium on charcoal in 4 ml of dimethylformamide is stirred at 140° C. for 4 hours. Subsequently, the mixture is worked up by adding diethyl ether and 2N hydrochloric acid, washing the separated organic phase with water and subsequently drying over anhydrous sodium sulphate, concentrating the organic phase under reduced pressure and recrystallizing the solid residue from ethanol. In this manner there is obtained p-methoxycinnamic acid in 65% yield. M.p. 170° C. (no depression upon mixing with a pure sample of this acid); 1H-NMR (CDCl3, 200 MHz): 3.85 ppm (s, 3H), 6.33 ppm (d, 15.5 Hz, 1H), 6.68-6.97 ppm (duplettoid, m 1H), 7.47-7.56 ppm (dupletteid m, 1H), 7.75 ppm (d, 15.5 Hz, 1H).

Workup

  1. washwashing the separated organic phase with water
  2. dry with materialsubsequently drying over anhydrous sodium sulphate
  3. concentrationconcentrating the organic phase under reduced pressure
  4. customrecrystallizing the solid residue from ethanol

Sources & evidence

ORD record
ord-ae91567b4e854d779c594baed2e76d94
Source dataset
uspto-grants-1995_10
Patent number
US05457226

Reaction notes

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