Reaction #64686

Reaction equation

formic acid

Meldrum's acid

veratraldehyde

triethylamine

→

3-(3,4-dimethoxyphenyl)propionic acid

Solvents

chloroform

Conditions

Workup

1. 1
   Otherprepared
2. 2
   Temperaturemaintained at the same temperature for further 1 hour
3. 3
   workup.DISTILLATIONThen the excess of formic acid and triethylamine was distilled off under reduced pressure of 2 kPa
4. 4
   Otherto give a distillate of 40 ml volume
5. 5
   Extractionextracted with 50 ml of 1N sodium hydroxide solution
6. 6
   ExtractionThe chloroform phase was extracted with 2×100 ml of 1N sodium hydroxide solution
7. 7
   Otherto give a yield of 8.6 g (81.8%), m.p.: 96°-97° C.

Procedure

After weighing 7.2 g (0.05 mol) of Meldrum's acid and 8.3 g (0.05 mol) of veratraldehyde to 50 ml of the mixture of formic acid and triethylamine prepared according to Example 1, the reaction mixture was heated to 100° C. during 1 hour and maintained at the same temperature for further 1 hour. Then the excess of formic acid and triethylamine was distilled off under reduced pressure of 2 kPa to give a distillate of 40 ml volume. The distillation residue was dissolved in 100 ml of chloroform and extracted with 50 ml of 1N sodium hydroxide solution. The chloroform phase was extracted with 2×100 ml of 1N sodium hydroxide solution. Thereafter Example 1 was followed to give a yield of 8.6 g (81.8%), m.p.: 96°-97° C.

Source