Hydrochloric Acid → 3-(3,5-Dimethoxyphenyl)prop-2-enoic acid

HRID 1069037Notes

Reaction equation

HRID 1069037 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[CH:6]=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.Cl>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:14][C:15]([OH:17])=[O:16])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 817473,5-Dimethoxybenzaldehyde

Product 1

HCID 860923-(3,5-Dimethoxyphenyl)prop-2-enoic acidYield 70.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3,5-dimethoxybenzaldehyde (12.5 g) in pyridine (20 ml) was added malonic acid (8.61 g) and piperidine (1 ml). The resulting solution was heated at 100° C. for 16 hours, cooled to room temperature, poured onto ice and acidified using conc. HCl. The resulting precipitate was collected, extracted into sodium bicarbonate solution and washed with isohexane. The aqueous phase was acidified using conc. HCl to yield a white precipitate which was filtered off, washed with water and dried to afford the subtitle compound (11.07 g).

Workup

  1. temperaturecooled to room temperature
  2. additionpoured onto ice
  3. customThe resulting precipitate was collected
  4. extractionextracted into sodium bicarbonate solution
  5. washwashed with isohexane
  6. customto yield a white precipitate which
  7. filtrationwas filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-1f56b13a2b604dc4a3ab0dc70a5ce3ea
Source dataset
uspto-grants-2001_06
Patent number
US06251910B1

Reaction notes

Loading…