4-Formylbenzoic acid → 4-(2-Ethoxycarbonyl-4-methyl-3-oxo-pent-1-enyl)benzoic acid

HRID 1162855Notes

Reaction equation

HRID 1162855 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:12]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)([OH:14])=[O:13]>>[CH2:10]([O:9][C:7]([C:6]([C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])=[CH:19][C:18]1[CH:21]=[CH:22][C:15]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1)=[O:8])[CH3:11]

Participants

3

Reactant 2

HCID 120884-Formylbenzoic acidHCID 81583Ethyl isobutyrylacetate

Product 1

HCID 671199894-(2-Ethoxycarbonyl-4-methyl-3-oxo-pent-1-enyl)benzoic acidYield 94%

Procedure

29.0 g of ethyl isobutyrylacetate and 33.0 g of 4-carboxybenzaldehyde are heated with a water trap for 6 h. The reaction solution is concentrated, taken up in ethyl acetate and extracted with 20% strength ammonium chloride solution and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate, concentrated and directly reacted further to 45. 50.0 g of an oil are obtained. C16H18O5 (290.3): MS (ESI+): 291.1 (M+H)+, tR=1.42 min (Gradient 2).

Workup

  1. concentrationThe reaction solution is concentrated
  2. extractionextracted with 20% strength ammonium chloride solution and saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customdirectly reacted further to 45

Sources & evidence

ORD record
ord-15a6a80222284e0f93bef66021bd6210
Source dataset
uspto-grants-2010_10
Patent number
US07820804B2

Reaction notes

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