Reaction #64697

Reaction equation

Meldrum's acid

formic acid

triethylamine

veratraldehyde

→

product

Yield 68.5%

3-(3,4-dimethoxyphenyl)propionic acid

Yield 68.5%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherprepared
2. 2
   workup.ADDITIONwere added to the reaction mixture
3. 3
   Temperaturerefluxing it for 4 hours
4. 4
   Otherthe acetonitrile was evaporated under reduced pressure

Procedure

After adding 2.1 ml of the mixture of formic acid and triethylamine prepared as described in Example 1 to 20 ml of acetonitrile, 3.60 g (0.025 mol) of Meldrum's acid and 4.15 g (0.025 mol) of veratraldehyde were added to the reaction mixture. After heating same to its boiling point (82° C.) within 30 minutes and refluxing it for 4 hours, the acetonitrile was evaporated under reduced pressure, then the method of Example 1 was followed to give 3.6 g of a product, m.p.: 91°-93.5° C., which was recrystallized from aqueous methanol of 50% by volume.

Source