Sulfuric Acid → HCID 20138676, compound

HRID 1253108Notes

Reaction equation

HRID 1253108 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]2[O:18][CH2:17][O:16][C:15]=12)[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=O.S(=O)(=O)(O)O.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:13]=[C:14]2[O:18][CH2:17][O:16][C:15]=12

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 13923414HCID 13923414, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20138676HCID 20138676, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 23938PalladiumCatalyst

Procedure

550 mg of methyl 3-methoxy-4,5-methylenedioxybenzoylacetate (10) and 55 mg of 5% Pd/C were suspended in 10 ml of methanol containing 2 drops (about 50 mg) of concentrated sulfuric acid. The mixture was subjected to hydrogenation at normal temperature and pressure. It was confirmed by thin layer chromatography that the hydrogenation was completed when twice as much moles of hydrogen as the starting material had been absorbed. After the catalyst was filtered out and washed, the filtrate was concentrated. The resultant residue was dissolved in 15 ml of ethyl ether, then dried over anhydrous magnesium sulfate, again filtered, washed with Et2O and concentrated to obtain 519 mg of pure methyl 3-(3-methoxy-4,5-methylenedioxyphenyl)propionate (12) with a quantitative yield.

Workup

  1. customhad been absorbed
  2. filtrationAfter the catalyst was filtered out
  3. washwashed
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe resultant residue was dissolved in 15 ml of ethyl ether
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationagain filtered
  8. washwashed with Et2O
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-38820e85710b48eea1798d55b26432d2
Source dataset
uspto-grants-1988_05
Patent number
US04746747

Reaction notes

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