Acetic Acid → HCID 131710703, compound

HRID 328159Notes

Reaction equation

HRID 328159 reaction equation
[CH2:1]([N:8]1[CH2:15][CH2:14][C:13]2([C:18]([O:20][CH3:21])=[O:19])[C:16](=[O:17])[CH:9]1[CH2:10][C:11]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:12]=12)C1C=CC=CC=1.[C:28]([OH:31])(=[O:30])[CH3:29].[H][H]>[Pd].C(O)CC>[C:18]([OH:20])(=[O:19])/[CH:13]=[CH:29]/[C:28]([OH:31])=[O:30].[C:18]([C:13]12[C:16](=[O:17])[CH:9]([CH2:10][C:11]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:12]=31)[N:8]([CH3:1])[CH2:15][CH2:14]2)([O:20][CH3:21])=[O:19]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 131710702HCID 131710702, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131710703HCID 131710703, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10311-PropanolSolvent

Procedure

Material V (0.01 m) in 50 ml. acetic acid was hydrogenated at 40 psi using 300 mg 10% palladium on carbon as catalyst until hydrogen uptake stopped (~100% theoretical observed). The catalyst was removed by filtration and the filtrate concentrated. The residue was treated with dilute potassium carbonate and extracted with methylene chloride to give an oil which was converted to a hydrogen fumarate salt in 1-propanol; mp 168°-171° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated
  3. additionThe residue was treated with dilute potassium carbonate
  4. extractionextracted with methylene chloride
  5. customto give an oil which

Sources & evidence

ORD record
ord-9ac0272ee10041f4bc6fa10675e3f8eb
Source dataset
uspto-grants-1977_04
Patent number
US04016167

Reaction notes

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