Hydrochloric Acid → 4-Carboxychalcone

HRID 77684Notes

Reaction equation

HRID 77684 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].[CH:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)=O.Cl>C(O)C.O>[C:18]([C:17]1[CH:21]=[CH:22][C:14]([CH:12]=[CH:2][C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])=[CH:15][CH:16]=1)([OH:20])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 120884-Formylbenzoic acidHCID 14798Sodium Hydroxide

Product 1

HCID 39957814-CarboxychalconeYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Acetophenone (44b, 0.50 ml, 4.3 mmol) and sodium hydroxide (0.50 g, 12.5 mmol) were combined in ethanol (2 ml) and water (2 ml) and stirred for 30 min at room temperature. 4-Formylbenzoic acid (1ad, 0.71 g, 4.7 mmol) was added and the mixture stirred for 48 hr at room temperature. Water (25 ml) was added, the mixture acidified with hydrochloric acid (1 N) and the resulting precipitate was filtered and recrystallized from ethyl acetate to give 0.65 g (60%) of a white solid: mp 222-224° C. [expected mp 227-229° C.]; 1H NMR: (DMSO) δ 7.67 (m, 4H), 7.99 (m, 4H), 8.18 (m, 3H), 13.14 (s, 1H); 13C NMR: (DMSO) δ 124.2, 128.5, 128.7, 128.8, 129.6, 132.1, 133.2, 137.3, 138.7, 142.4, 166.7, 189.0.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-445a5cd8524447229ac2ddcc1f9aaa3a
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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