Acetic Acid → 3,3'-Dicarboxychalcone

HRID 1987715Notes

Reaction equation

HRID 1987715 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=C(C#N)[CH:14]=2)=[O:12])[CH:6]=[CH:7][CH:8]=1)#N.[OH:21]S(O)(=O)=O.[OH2:26].[C:27]([OH:30])(=[O:29])[CH3:28]>>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:28]([C:27]([OH:30])=[O:29])[CH:14]=2)=[O:12])[CH:6]=[CH:7][CH:8]=1)([OH:21])=[O:26]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 544082233,3'-Dicyanochalcone

Product 1

HCID 538375063,3'-Dicarboxychalcone

Procedure

A solution of 3,3′-dicyanochalcone from step 1 (2.0 g, 7.75 mmol) in glacial acetic acid (30 mL) was treated with a mixture of concentrated H2SO4 (10 mL) and water (10 mL). The reaction mixture was heated to 130 C for 12 hours, cooled to room temperature and filtered. The precipitate was washed with water (3×100 mL) and dried in vacuo to give 3,3′-dicarboxychalcone as a yellow solid. MS (APCI) m/z 295 (M+−1, 100%). 13C NMR (50 MHz, d6-DMSO); δ 122.5, 128.6, 128.7, 129.2, 130.8, 131.0, 131.2, 132.4, 132.5, 133.1, 134.5, 137.2, 143.1, 166.3, 166.5, 188.2

Workup

  1. temperatureThe reaction mixture was heated to 130 C for 12 hours
  2. filtrationfiltered
  3. washThe precipitate was washed with water (3×100 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7a713105e2f440ac98c33e966174f3d7
Source dataset
uspto-grants-2009_06
Patent number
US07553809B2

Reaction notes

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