Benzaldehyde → 1-(4-Carboxyphenyl)-3-phenyl-2-propen-1-one

HRID 77681Notes

Reaction equation

HRID 77681 reaction equation
[OH-:1].[Na+].[CH2:3]([OH:5])[CH3:4].[CH:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl>O>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([C:3](=[O:5])[CH:4]=[CH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:9][CH:8]=1)([OH:1])=[O:13]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium Hydroxide

Product 1

HCID 544932011-(4-Carboxyphenyl)-3-phenyl-2-propen-1-oneYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Acetylbenzonitrile (44al, 1.00 g, 6.9 mmol) and sulfuric acid (4 ml) were combined in water (4 ml) and the mixture stirred for 2.5 hr at reflux. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to give 0.98 g (87%) of compound 44ad as a white solid: mp 204° C.; 1H NMR: (DMSO) δ 2.61 (s, 3H), 8.04 (s, 4H), 13.23 (s, 1H). The solid (44ad, 0.50 g, 3.0 mmol) and sodium hydroxide (0.29 g, 7.3 mmol) were combined in water (4 ml) and ethanol (4 ml) and stirred for 30 min at room temperature. Benzaldehyde (1b, 0.31 ml, 3.1 mmol) was added and the mixture stirred for 48 hr at room temperature. The resulting mixture was acidified with hydrochloric acid (1 N), extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to a afford a solid. The crude solid was recrystallized from ethyl acetate to give 0.54 g (70%) of a yellow solid: mp 217-220° C. [expected mp 217-220° C.]; 1H NMR: (DMSO) δ 7.45 (m, 5H), 7.76 (d, 1H, J=16.1 Hz), 7.93 (d, 1H, J=15.5 Hz), 8.09 (d, 2H, J=7.9 Hz), 8.23 (d, 2H, J=7.6 Hz) 13.34 (s, 1H); 13C NMR: (DMSO) δ 121.9, 128.5, 128.8, 128.9, 129.4, 130.6, 134.3, 134.4, 140.6, 144.6, 166.4, 188.8.

Workup

  1. extractionextracted into ethyl acetate
  2. washwashed with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to
  6. customa afford a solid
  7. customThe crude solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a393e187a88a47ecba4ebae04d99f937
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

Loading…