3-Phenylprop-2-Enal → HCID 13595926, compound

HRID 566444Notes

Reaction equation

HRID 566444 reaction equation
[CH:1](=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][NH:18][CH3:19]>CCOCC>[CH3:17][N:18]([CH3:19])/[CH:1]=[CH:2]/[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 674DimethylamineHCID 11430Potassium Carbonate

Product 1

HCID 13595926HCID 13595926, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-60 °C

Procedure

A mixture of 19.6 mL (20.0 grams, 149 mmol) of cinnamaldehyde, 40.6 grams (298 mmol) of potassium carbonate, and 150 mL of ether was cooled to −60° C. and treated with a prechilled (−78° C.) solution of 17.8 mL (13.5 grams, 300 mmol) of liquid dimethylamine, condensed from the gas at −78° C., in 20 mL of ether. After stirring for 0.5 hours at −60° C., the mixture was allowed to slowly warm to room temperature and then stirred for an additional 3 hours. The mixture was filtered, concentrated, and distilled to give 10.2 grams (42% yield) of the title compound as a yellow liquid, bp 95-100° C./2.8-3.0 Torr. The liquid slowly polymerized on standing and was used directly. 1H NMR (CDCl3) d 2.57 (6H, s), 3.30 (2H, d, J=7 Hz), 4.35 (1H, dt, J=7, 14 Hz), 5.99 (1H, dt, J=1, 14 Hz), 7.15-732 (5H, m).

Workup

  1. temperatureto slowly warm to room temperature
  2. stirringstirred for an additional 3 hours
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-0e6b9ffedce5407786230452aa7b2739
Source dataset
uspto-grants-2001_01
Patent number
US06174895B1

Reaction notes

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