HCID 10366489, compound → HCID 10428576, compound

HRID 1647026Notes

Reaction equation

HRID 1647026 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][CH:5]=[C:6]([C:30]([O:32][CH3:33])=[O:31])[C:7]=2[C:10]2[C:11]([C:26]([O:28][CH3:29])=[O:27])=[CH:12][C:13]([O:24][CH3:25])=[C:14]([O:16]CC3C=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:30]([O:32][CH3:33])=[O:31])[C:7]=2[C:10]2[C:11]([C:26]([O:28][CH3:29])=[O:27])=[CH:12][C:13]([O:24][CH3:25])=[C:14]([OH:16])[CH:15]=2)[O:2]1

Participants

6

Reactant 2

HCID 10366489HCID 10366489, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10428576HCID 10428576, compoundYield 93.5%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl 5,6-methylenedioxy-4'-methoxy-5'-benzyloxy-2,2'-biphenyldicarboxylate (1.15 g) is dissolved in tetrahydrofuran (50 ml) and methanol (50 ml), and the solution is sitrred 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'-biphenyldicarboxylate (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-fded4b24d3314ffd876c50757d7cbb32
Source dataset
uspto-grants-1993_01
Patent number
US05182404

Reaction notes

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