Toluene → HCID 20319779, compound

HRID 866582Notes

Reaction equation

HRID 866582 reaction equation
C1(C)C=CC=CC=1.[C:8]([CH2:12][CH2:13][CH2:14][C:15]1[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=1[CH2:17][CH:18]1[C:22](=[O:23])[C:21](=[O:24])[CH2:20][C:19]1=[O:25])([O:10][CH3:11])=[O:9]>CC(O)C.[Pd]>[C:8]([CH2:12][CH2:13][CH2:14][C:15]1[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=1[CH2:17][CH:18]1[C:22](=[O:23])[CH:21]([OH:24])[CH2:20][C:19]1=[O:25])([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 1140TolueneHCID 20305123HCID 20305123, compound

Product 1

HCID 20319779HCID 20319779, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A toluene solution of 30.5 g (0.1 mol) of 2-[2-(3-carbomethoxypropyl)benzyl]-1,3,4-cyclopentanetrione, XIIa, was thoroughly dried by azeotropic distillation. Removal of the toluene gave a red oil that was taken up in 200 ml of 2-propanol. Five grams of Pd/C was added and the compound hydrogenated at 0.25 psi for 3 days. The catalyst was filtered and the solvent evaporated to give the crude product. This was chromatographed on silicic acid and eluted with 4:1 benzene:ethyl acetate. The major fraction amounted to 20 g of the hydroxy dione XIIIa as a clear, light tan oil.

Workup

  1. customRemoval of the toluene
  2. customgave a red oil that
  3. filtrationThe catalyst was filtered
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-6fab4d26690344daaeba07f3f9865fa4
Source dataset
uspto-grants-1978_07
Patent number
US04100185

Reaction notes

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