Formic Acid → 3-(3,4-Dimethoxyphenyl)propionic acid
Reaction equation
CC1(C)[O:9][C:7](=[O:8])[CH2:6][C:4](=O)O1.C(=O)[C:12]1[CH:21]=[CH:20][C:17]([O:18][CH3:19])=[C:14]([O:15][CH3:16])[CH:13]=1.C(O)=O.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:16][O:15][C:14]1[CH:13]=[C:12]([CH2:4][CH2:6][C:7]([OH:9])=[O:8])[CH:21]=[CH:20][C:17]=1[O:18][CH3:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °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 1 N sodium hydroxide solution. The chloroform phase was extracted with 2×100 ml of 1 N sodium hydroxide solution. Thereafter Example 1 was followed to give a yield of 8.6 g (81.8%), m.p.: 96°-97° C.
Workup
- customprepared
- temperaturemaintained at the same temperature for further 1 hour
- distillationThen the excess of formic acid and triethylamine was distilled off under reduced pressure of 2 kPa
- customto give a distillate of 40 ml volume
- extractionextracted with 50 ml of 1 N sodium hydroxide solution
- extractionThe chloroform phase was extracted with 2×100 ml of 1 N sodium hydroxide solution
- customto give a yield of 8.6 g (81.8%), m.p.: 96°-97° C.
Sources & evidence
- ORD record
- ord-8a7851c5d0b448429c13246926258c39
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05350872
Reaction notes
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