Toluene → 4-Ethenylphenyl acetate

HRID 2224011Notes

Reaction equation

HRID 2224011 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]([C:10](C#N)=C)=[O:9].[C:14]1(C)C=CC=C[CH:15]=1>>[C:8]([O:7][C:6]1[CH:1]=[CH:2][C:3]([CH:14]=[CH2:15])=[CH:4][CH:5]=1)(=[O:9])[CH3:10]

Participants

3

Reactant 2

HCID 1140TolueneHCID 77126Hexyl 2-cyanoprop-2-enoate2×

Product 1

HCID 758214-Ethenylphenyl acetate

Procedure

The purpose of this prophetic Example is to demonstrate the chemical derivatization of pHS in the organic extractant from the biphasic reaction medium to form the derivatized compound para-acetoxystyrene. The pHCA is first produced by fermentation using a recombinant strain of E. coli. The bio-produced pHCA is then converted to pHS in a biphasic reaction medium, consisting of fermentation supernatant and toluene, using PDC2 cell-free extract. After the toluene layer is separated from the pHCA-depleted fermentation supernatant, the bio-produced pHS is reacted with acetic anhydride to form para-acetoxystyrene.

Workup

  1. customAfter the toluene layer is separated from the pHCA-
  2. customthe bio-produced pHS is reacted with acetic anhydride

Sources & evidence

ORD record
ord-dff2b47feb3c4ab1b6f4db3e06f878f1
Source dataset
uspto-grants-2008_05
Patent number
US07378261B2

Reaction notes

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