Toluene → 5-[(Z)-3-ethoxy-2-isopropoxy-3-oxo-1-propenyl]-2-methoxybenzoic acid

HRID 1816558Notes

Reaction equation

HRID 1816558 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:6][C:7]1[CH:8]=[CH:9][C:10]([O:20][CH3:21])=[C:11]([CH:19]=1)[C:12]([O:14]C(C)(C)C)=[O:13])[CH3:2].FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[CH2:1]([O:3][C:4](=[O:26])/[C:5](/[O:22][CH:23]([CH3:25])[CH3:24])=[CH:6]/[C:7]1[CH:8]=[CH:9][C:10]([O:20][CH3:21])=[C:11]([CH:19]=1)[C:12]([OH:14])=[O:13])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 69800512Tert-butyl 5-(3-ethoxy-2-isopropoxy-3-oxo-1-propenyl)-2-methoxybenzoate

Product 1

HCID 599979455-[(Z)-3-ethoxy-2-isopropoxy-3-oxo-1-propenyl]-2-methoxybenzoic acidYield 25.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.3 g of tert-butyl 5-(3-ethoxy-2-isopropoxy-3-oxo-1-propenyl)-2-methoxybenzoate was dissolved in 2.5 ml dichloromethane, and 1.2 ml trifluoroacetic acid was added under ice-cooling, and the mixture was stirred as such under ice-cooling for 2 hours. 30 ml toluene was added to the reaction mixture and the solvent was evapoarated; this procedure was repeated twice. Then, the residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (2:1), 65 mg of 5-[(Z)-3-ethoxy-2-isopropoxy-3-oxo-1-propenyl]-2-methoxybenzoic acid was obtained.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hours
  3. washfrom fractions eluted with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-0615f9d3e06941dcb19937e777a36cd7
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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