Dimethylacetamide → Butyl 3-(4-formylphenyl)prop-2-enoate

HRID 2228813Notes

Reaction equation

HRID 2228813 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(C1C=CC=[C:16]([C:20]([CH3:23])(C)C)[C:15]=1[OH:24])(C)(C)C.[C:25]([O-:28])(=O)[CH3:26].[Na+].[CH3:30]C(N(C)C)=O>O>[CH2:15]([O:24][C:25](=[O:28])[CH:26]=[CH:30][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[CH2:16][CH2:20][CH3:23]

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 314052,6-Di-tert-butylphenolHCID 707414-BromobenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 53816893Butyl 3-(4-formylphenyl)prop-2-enoateYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20.4 g (110 mmol) of 4-bromobenzaldehyde A1, 19.7 g (154 mmol) of nbutylacrylate D1, 10 mg (0.05 mmol) of 2,6-di- tert-butylphenol and 9.9 g (120 mmol) of sodium acetate are mixed with 200 ml of dimethylacetamide and, after adding 5 ppm each of the catalysts K1-K11 (1.2), are stirred for 90 minutes at 190° C. in an oil bath. The mixture is worked up in water and extracted with ether. The organic phases are washed several times with water and are filtered through silica gel. The solvent is evaporated, giving 4-formylcinnamic acid-n-butyl ester C25 (purity>99% GC) without any purification in a yield of >95%. Analytical data identical with the described data (J. Organomet. Chem, 1995, 491, 1-2, C1; Angew. Chem., 1995, 107, 1989). Molecular mass C14H16O3: 232.28; calcd. C: 72.39%, H: 6.94%; found C: 72.46%, H: 7.00%.

Workup

  1. additionafter adding 5 ppm each of the catalysts
  2. extractionextracted with ether
  3. washThe organic phases are washed several times with water
  4. filtrationare filtered through silica gel
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-9a8a1307f90a489787e3c9808466a033
Source dataset
uspto-grants-2002_07
Patent number
US06417357B1

Reaction notes

Loading…