Pyridine → 3,5-Diacetoxy Styrene

HRID 1163267Notes

Reaction equation

HRID 1163267 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[C:8]([O:11][CH2:12][CH3:13])(=[O:10])[CH3:9].N1C=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:5]([O:4][C:1]1[CH:15]=[C:16]([CH:13]=[C:12]([O:11][C:8](=[O:10])[CH3:9])[CH:2]=1)[CH:17]=[CH2:18])(=[O:7])[CH3:6]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl Acetate

Product 1

HCID 113105593,5-Diacetoxy StyreneYield 87%

Procedure

The product mixture was solved in 10 ml of pyridine and treated with 2.33 ml (21.2 mmol) of acetic anhydride without further purification for 15 h at room temperature. The resulting solution was poured into 100 ml ethyl acetate and extracted three times against 100 ml of 1N HCl. The organic layer washed twice with 50 ml of brine and dried over MgSO4. After evaporation of the solvent chromatographic purification over silica gel using a 7:2 (v/v) mixture of n-hexane and ethyl acetate gave 8.04 g of 3,5-diacetoxystyrene as a colorless oil (36.5 mmol, 87%).

Workup

  1. extractionextracted three times against 100 ml of 1N HCl
  2. washThe organic layer washed twice with 50 ml of brine
  3. dry with materialdried over MgSO4
  4. customAfter evaporation of the solvent chromatographic purification over silica gel using
  5. additiona 7:2 (v/v) mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-9894eec3154d4ccea3cda994845642bd
Source dataset
uspto-grants-2010_10
Patent number
US07820848B2

Reaction notes

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