Methane → 3,4,5-Trimethoxyhydrocinnamic acid

HRID 990307

Reaction equation

HRID 990307 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:19](=C)[C:20](O)=O)[CH:12]=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16].C>[Pd].O>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([CH2:19][CH2:20][C:1]([OH:2])=[O:4])[CH:10]=[C:9]([O:8][CH3:7])[C:14]=1[O:15][CH3:16]

Participants

6

Reactant 3

HCID 297MethaneHCID 11430Potassium CarbonateHCID 208491922-(3,4,5-Trimethoxyphenyl)prop-2-enoic acid

Product 1

HCID 648603,4,5-Trimethoxyhydrocinnamic acidYield 167.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

6.8 g of potassium carbonate is added to a solution of 21.44 g of 3,4,5-trimethoxyphenylpropenoic acid and 45 ml of water then the medium is hydrogenated for one hour under a pressure of 1200-1300 mbars in the presence of 1.8 g activated charcoal with 10% palladium, in this way 2.1 l of hydrogen is absorbed. The reaction medium is filtered, followed by washing with water and acidifying with 50 ml of hydrochloric acid (2N). After separation, the residue is washed with water and dried under reduced pressure at ambient temperature. In this way 19.8 g of the expected product is obtained (M.P.=102-103° C.)

Workup

  1. customin this way 2.1 l of hydrogen is absorbed
  2. filtrationThe reaction medium is filtered
  3. washby washing with water and acidifying with 50 ml of hydrochloric acid (2N)
  4. customAfter separation
  5. washthe residue is washed with water
  6. customdried under reduced pressure at ambient temperature

Sources & evidence

ORD record
ord-1520d5cc440741be96bb0ab6200a861d
Source dataset
uspto-grants-2002_10
Patent number
US06459001B1

Linked notes

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