Methane → 3,4,5-Trimethoxyhydrocinnamic acid

HRID 619773

Reaction equation

HRID 619773 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.[H][H]>[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

7

Reactant 4

HCID 297MethaneHCID 11430Potassium CarbonateHCID 208491922-(3,4,5-Trimethoxyphenyl)prop-2-enoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 648603,4,5-Trimethoxyhydrocinnamic acidYield 167.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

6.8 g of potassium carbonate were added to a solution of 21.44 g of 3,4,5-trimethoxyphenylpropenoic acid and 45 ml of water and the mixture was hydrogenated for one hour under a pressure of 1200-1300 mbar in the presence of 1.8 g of activated charcoal with 10% of palladium during which 2.1 liters of hydrogen were absorbed. Filtration was carried out, followed by washing with water and acidifying with 50 ml of hydrochloric acid (2 N). The product was separated off, washed with water and dried under reduced pressure at ambient temperature to obtain 19.8 g of the expected product melting at 102-103° C.

Workup

  1. customwere absorbed
  2. filtrationFiltration
  3. washby washing with water and acidifying with 50 ml of hydrochloric acid (2 N)
  4. customThe product was separated off
  5. washwashed with water
  6. customdried under reduced pressure at ambient temperature

Sources & evidence

ORD record
ord-033cea20126547ecb64b172b41af589d
Source dataset
uspto-grants-1999_09
Patent number
US05959146

Linked notes

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