Hydrochloric Acid → Cinnamoylbenzene

HRID 473064Notes

Reaction equation

HRID 473064 reaction equation
CO[C:3]1[CH:4]=[C:5]([CH:8]=[C:9](OC)[C:10]=1OC)[CH:6]=[O:7].[CH3:15][C:16]([C:18]1[CH:23]=[C:22](OC)[C:21](OC)=[C:20](OC)[CH:19]=1)=O.Cl>C(=O)([O-])[O-].[K+].[K+].O>[C:18]1([CH:16]=[CH:15][C:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:3][CH:4]=2)=[O:7])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68583,4,5-Trimethoxybenzaldehyde2×HCID 143453',4',5'-Trimethoxyacetophenone

Product 1

HCID 7189Cinnamoylbenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a stirred solution of 3,4,5-trimethoxybenzaldehyde (190 mg, formula 5) in 10% methanolic potassium carbonate (15 mL), 3,4,5-trimethoxyacetophenone (200 mg) was added. It was stirred for 3 hours. On completion, the reaction mixture was diluted with water, acidified with dil. HCl and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulphate and evaporated to get a residue. The residue was purified through silica gel column to get chalcone of formula 6 (240 mg)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated
  5. customto get a residue
  6. customThe residue was purified through silica gel column

Sources & evidence

ORD record
ord-0c93a4b94d1a437bbadeef6314b011a7
Source dataset
uspto-grants-2014_01
Patent number
US08633242B2

Reaction notes

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