Hydrochloric Acid → 2',5'-Dimethoxycinnamic acid

HRID 465952Notes

Reaction equation

HRID 465952 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH:5]=O.N1CCCCC1.C(O)(=O)[CH2:20][C:21]([OH:23])=[O:22].Cl>N1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1/[CH:5]=[CH:20]/[C:21]([OH:23])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 667262,5-Dimethoxybenzaldehyde

Product 1

HCID 6975942',5'-Dimethoxycinnamic acidYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

2,5-Dimethoxybenzaldehyde (1.7 g) was dissolved in pyridine (10 ml). Piperidine (0.2 ml) and malonic acid (2.0 g) were added to the solution. The solution was stirred for 1 hour at 85° C. and then for 3 hr. at 110° C. The solution was cooled. Water (80 ml) was added to the solution. Conc. hydrochloric acid was added to the solution until pH of the solution was down to about 2. The crystals were deposited. The crystals were separated from the solution by filtration, washed with water and dried to give the title compound (1.97 g) having the following physical data.

Workup

  1. waitfor 3 hr
  2. customat 110° C
  3. temperatureThe solution was cooled
  4. customThe crystals were separated from the solution by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-b23ea8db51694bcab66481c55d67b900
Source dataset
uspto-grants-1992_10
Patent number
US05155104

Reaction notes

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