1-(1-Acetoxyethyl)-3,5-diacetoxy-benzene → 3,5-Diacetoxy Styrene

HRID 1163268Notes

Reaction equation

HRID 1163268 reaction equation
C(O[CH:5]([C:7]1[CH:12]=[C:11]([O:13][C:14](=[O:16])[CH3:15])[CH:10]=[C:9]([O:17][C:18](=[O:20])[CH3:19])[CH:8]=1)[CH3:6])(=O)C>C1(C)C=CC=CC=1>[C:14]([O:13][C:11]1[CH:12]=[C:7]([CH:8]=[C:9]([O:17][C:18](=[O:20])[CH3:19])[CH:10]=1)[CH:5]=[CH2:6])(=[O:16])[CH3:15]

Participants

3

Reactant 1

HCID 117375661-(1-Acetoxyethyl)-3,5-diacetoxy-benzene

Product 1

HCID 113105593,5-Diacetoxy StyreneYield 42.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
500 °C

Procedure

20 g of 1-(1-acetoxyethyl)-3,5-diacetoxy-benzene (71 mmol) were dissolved in 20 ml toluene and placed into a feed vessel connected to a pyrolytic tube filled with Raschig rings. The tube was heated to 500° C. and the neat mixture was immediately added. Conversion of the alcohol was achieved within two minutes. The column was rinsed with toluene. Work-up was conducted by extracting the crude material in toluene twice with 200 ml water. The aqueous solutions were reextracted with toluene, the organic layers were combined, dried over magnesium sulfate and the solvent removed under reduced pressure giving 6.6 g 3,5-diacetoxystyrene (42%).

Workup

  1. customplaced into a feed vessel
  2. customconnected to a pyrolytic tube
  3. additionfilled with Raschig rings
  4. additionthe neat mixture was immediately added
  5. washThe column was rinsed with toluene
  6. extractionby extracting the crude material in toluene twice with 200 ml water
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4384818e26ee41f096313884190b9ad7
Source dataset
uspto-grants-2010_10
Patent number
US07820848B2

Reaction notes

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