HCID 54127777, compound → 2-(4-Methylbenzyl)succinic acid

HRID 1590171Notes

Reaction equation

HRID 1590171 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]=[C:7]([CH2:11][C:12]([OH:14])=[O:13])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]([CH2:11][C:12]([OH:14])=[O:13])[C:8]([OH:10])=[O:9])=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 54127777HCID 54127777, compound

Product 1

HCID 955572-(4-Methylbenzyl)succinic acidYield 94.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 2-(4-methylbenzylidene)succinic acid (4.5 g) in ethanol (50 ml) was added 10% Pd-C (100 mg) and the mixture was hydrogenated at room temperature and atmospheric pressure for 40 hours. After the catalyst was filtered off, the solvent was evaporated under reduced pressure. The resulting residue was recrystallized from hexane-ethyl acetate (1:1) to give 4.3 g of 2-(4-methylbenzyl)succinic acid.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationAfter the catalyst was filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was recrystallized from hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-5209051602b6482a9df3e88a406df5cc
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

Loading…