3-Phenylprop-2-Enal → HCID 72281739, compound

HRID 1923466Notes

Reaction equation

HRID 1923466 reaction equation
[OH-:1].[Na+].[CH:3](=O)[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)(=O)[CH3:14].Cl>O.C(O)C>[O:1]=[C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:4]=[CH:3][CH:14]=[CH:13][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 3073-Phenylprop-2-EnalHCID 313Hydrochloric AcidHCID 114704-Acetylbenzoic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 72281739HCID 72281739, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

Sodium hydroxide (128.0 g, 3.2 mol) is dissolved in water (1400 mL) and ethanol (675 mL). Cinnamaldehyde (66.1 g, 0.5 mol) and 4-acetylbenzoic acid (82.1 g, 0.5 mol) are added and the mixture stirred for about 5 min. A thick precipitate is formed and the thick mixture is diluted with water (750 mL) and ethanol (750 mL). Stir at room temperature for 18 h. The reaction is cooled and acidified with concentrated HCl (270 mL). The mixture is extracted with ethyl acetate (3×). The combined organic portions are washed with water (2×), dried over Na2SO4, filtered and evaporated. The resulting solid is recrystallized from 2-methoxyethanol and washed with diethyl ether to obtain 36.1 g (26%) of yellow crystals. m.p.=210-214° C.; Anal. Calcd for C18H14O3: C, 77.68; H, 5.07. Found: C, 77.47; H, 5.09.

Workup

  1. customA thick precipitate is formed
  2. stirringStir at room temperature for 18 h
  3. temperatureThe reaction is cooled
  4. extractionThe mixture is extracted with ethyl acetate (3×)
  5. washThe combined organic portions are washed with water (2×)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe resulting solid is recrystallized from 2-methoxyethanol
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-ab64cbaa2ac148b2bb05369a76638240
Source dataset
uspto-grants-2012_05
Patent number
US08178528B2

Reaction notes

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