3,5-Dimethoxystyrene → Benzene, 1,3-dimethoxy-5-ethyl

HRID 1003949Notes

Reaction equation

HRID 1003949 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=[CH2:7]>CO.C(OCC)(=O)C.[C].[Pd]>[CH3:12][O:11][C:9]1[CH:8]=[C:5]([CH2:6][CH3:7])[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=1

Participants

5

Reactant 1

HCID 98152983,5-Dimethoxystyrene

Product 1

HCID 524877Benzene, 1,3-dimethoxy-5-ethylYield 84.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,5-Dimethoxystyrene (8.29 g) is dissolved in a mixture of methanol (70 ml) and ethyl acetate (10 ml), and the mixture is subjected to catalytic hydrogenation with using 10% palladium-carbon (51.4% aqueous, 1.2 g) under atmospheric pressure. One hour thereafter, the catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate) to give 1,3-dimethoxy-5-ethylbenzene (7.07 g).

Workup

  1. customOne hour thereafter, the catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2699772df4f44ca88778c0773a3eadb0
Source dataset
uspto-grants-2000_04
Patent number
US06048842

Reaction notes

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