HCID 15670669, compound → HCID 10428576, compound

HRID 2253884Notes

Reaction equation

HRID 2253884 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][CH:5]=[C:6]([C:31]([O:33][CH3:34])=[O:32])[C:7]=2[C:10]2[C:11]([C:27]([O:29][CH3:30])=[O:28])=[CH:12][C:13]([O:25][CH3:26])=[C:14]([O:16]C(=O)C3C=CC=CC=3)[CH:15]=2)[O:2]1.[H][H]>O1CCCC1.CO.[C].[Pd]>[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][CH:5]=[C:6]([C:31]([O:33][CH3:34])=[O:32])[C:7]=2[C:10]2[C:11]([C:27]([O:29][CH3:30])=[O:28])=[CH:12][C:13]([O:25][CH3:26])=[C:14]([OH:16])[CH:15]=2)[O:2]1

Participants

6

Reactant 2

HCID 15670669HCID 15670669, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10428576HCID 10428576, compoundYield 96.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl 5,6-methylenedioxy-4'-methoxy-5'-benzoyloxy-2,2'-biphenyldicarboxylate (1.15 g) is dissolved in tetrahydrofuran (50 ml) and methanol (50 ml), and the solution is stirred under 40 psi hydrogen gas atmosphere in the presence of palladium-carbon (0.2 g) for 16 hours. After the reaction, the catalyst is filtered off, and the filtrate is evaporated into dryness under reduced pressure. The residue is treated with methanol to give dimethyl 5,6-methylenedioxy-4'-methoxy-5'-hydroxy-2,2'-biphenyl-dicarboxylate (0.86 g) as colorless crystal. M.p. 172°-173° C.

Workup

  1. customAfter the reaction
  2. filtrationthe catalyst is filtered off
  3. customthe filtrate is evaporated into dryness under reduced pressure
  4. additionThe residue is treated with methanol

Sources & evidence

ORD record
ord-93096e6aa7384d66aa9c26c1032adc4b
Source dataset
uspto-grants-1993_08
Patent number
US05233057

Reaction notes

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