Sodium Chloride → 4-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde

HRID 359635

Reaction equation

HRID 359635 reaction equation
C([O:4][CH2:5][CH2:6][N:7]([C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1)[CH2:8][CH3:9])(=O)C.[Br-].[O:19]1CCO[CH:20]1[CH2:24][P+](CCCC)(CCCC)CCCC.CC(C)([O-])C.[K+].[Cl-].[Na+]>CN(C)C=O.Cl.O>[OH:4][CH2:5][CH2:6][N:7]([C:10]1[CH:11]=[CH:12][C:13]([CH:14]=[CH:24][CH:20]=[O:19])=[CH:16][CH:17]=1)[CH2:8][CH3:9]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 11458991Benzaldehyde, 4-[[2-(acetyloxy)ethyl]ethylamino]-HCID 22292430Tributyl(1,3-dioxolan-2-ylmethyl)phosphonium BromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 544515964-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 235.3 g (1 mole) of 4-(N-2-acetoxyethyl-N-ethylamino)benzaldehyde in dimethylformamide is added 738.7 g (2.0 moles) of 1,3-dioxolan-2-ylmethyltributylphosphonium bromide in dimethylformamide, and the mixture is heated at 90° C. Potassium t-butoxide (224.4 g, 2.0 moles) is added, and heating is continued at 90° C. for 16 hours. After cooling to room temperature, the solution is poured into a seven-fold excess of water, the aqueous mixture is saturated with sodium chloride, and the solution is extracted with three portions of ether. The combined organics are dried over 4A sieves, filtered through cotton, and evaporated. The crude reaction product is dissolved in 3M HCl, and the reaction is stirred at room temperature for 16 hours. After neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether, and the combined organics are dried over 4A sieves, filtered through cotton, and evaporated to yield the cinnamaldehyde as an oil. The product is purified by flash chromatography (silica gel, 1:1 hexane:ethyl acetate).

Workup

  1. temperatureheating
  2. temperatureAfter cooling to room temperature
  3. extractionthe solution is extracted with three portions of ether
  4. dry with materialThe combined organics are dried over 4A sieves
  5. filtrationfiltered through cotton
  6. customevaporated
  7. customThe crude reaction product
  8. extractionAfter neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether
  9. dry with materialthe combined organics are dried over 4A sieves
  10. filtrationfiltered through cotton
  11. customevaporated

Sources & evidence

ORD record
ord-86fa6da997994c81b205357250765256
Source dataset
uspto-grants-1991_03
Patent number
US05002361

Linked notes

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