Methyl isoeugenol → 1,2-Dimethoxy-4-propylbenzene

HRID 704000

Reaction equation

HRID 704000 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][CH3:11])=[CH:5][C:4]=1[O:12][CH3:13].[H][H]>[Pd].CO>[CH2:9]([C:6]1[CH:5]=[C:4]([O:12][CH3:13])[C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH2:10][CH3:11]

Participants

5

Reactant 2

HCID 7128Methyl isoeugenolHCID 178418361HCID 178418361, compound

Product 1

HCID 1232331,2-Dimethoxy-4-propylbenzeneYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

An atmospheric pressure hydrogenation equipment was charged with 17.8 g (0.10 M) of 1,2-dimethoxy-4-propenylbenzene, 0.9 g of palladium charcoal and 350 ml of methanol and introduced with hydrogen. The reaction was continued until the absorption of hydrogen was terminated. Palladium charcoal was filtered off from the reaction mixture. The filtrate was distilled off methanol and vacuum distilled to obtain 17.5 g (0.097 M) of 4-propylveratrole as colorless transparent liquid having a boiling point of 106°-108° C./4 mmHg.

Workup

  1. customThe reaction was continued until the absorption of hydrogen
  2. customwas terminated
  3. filtrationPalladium charcoal was filtered off from the reaction mixture
  4. distillationThe filtrate was distilled off methanol and vacuum
  5. distillationdistilled

Sources & evidence

ORD record
ord-403b7e4fe4dd478fa644cd46e92ab690
Source dataset
uspto-grants-1991_01
Patent number
US04985458

Linked notes

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