3,5-Diacetoxy Styrene → 1,3-Diacetoxy-5-ethylbenzene

HRID 1003947Notes

Reaction equation

HRID 1003947 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:13][C:14](=[O:16])[CH3:15])[CH:12]=1)[CH:8]=[CH2:9])(=[O:3])[CH3:2]>C(OCC)(=O)C.C(O)C.[C].[Pd]>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:8][CH3:9])[CH:10]=[C:11]([O:13][C:14](=[O:16])[CH3:15])[CH:12]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 1

HCID 113105593,5-Diacetoxy Styrene

Product 1

HCID 220166621,3-Diacetoxy-5-ethylbenzeneYield 76.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,5-Diacetoxystyrene (580 mg) is dissolved in a mixture of ethyl acetate (6 ml) and ethanol (2 ml), and the mixture is subjected to catalytic reduction with using 10% palladium-carbon (51.4% aqueous, 50 mg) under atmospheric pressure. Two hours 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-diacetoxy-5-ethylbenzene (450 mg).

Workup

  1. customTwo hours 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-d555f42b89c445948a1062faf84a7786
Source dataset
uspto-grants-2000_04
Patent number
US06048842

Reaction notes

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