Benzaldehyde → HCID 244688, compound

HRID 1954024Notes

Reaction equation

HRID 1954024 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.[OH-].[Ba+2].[OH-].Cl>C(O)C>[OH:10][C:8]1[CH:9]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:2](=[O:3])[CH:1]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 84873-HydroxyacetophenoneHCID 17749100Barium hydroxide, monohydrate

Product 1

HCID 244688HCID 244688, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 250 ml round bottom flask equipped with a magnetic stirrer and reflux condenser, was charged 2.7 g (0.02 moles) of 3-hydroxyacetophenone, 2.1 g (0.02 moles) of benzaldehyde, 2.0 g (0.011 moles) of barium hydroxide, monohydrate, and 20 ml of absolute ethanol. The reaction mixture was refluxed for a total of 2.5 hours, after which it became thick and difficult to stir. Upon cooling, the resulting solid was dissolved in 100 ml. of 1 N aqueous hydrochloric acid, and another solid was observed to precipitate from this solution. The solid was collected by vacuum filtration, and washed with 100 ml. of water, then 100 ml. of hexane and dried in vacuuo at 40° C. for 24 hours. As a result, 4.2 g (93% yield) of 3'-hydroxychalcone was isolated as a tan solid, MP=143-147° C.

Workup

  1. customTo a 250 ml round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was refluxed for a total of 2.5 hours
  4. temperatureUpon cooling
  5. dissolutionthe resulting solid was dissolved in 100 ml
  6. customto precipitate from this solution
  7. filtrationThe solid was collected by vacuum filtration
  8. washwashed with 100 ml
  9. dry with materialof hexane and dried in vacuuo at 40° C. for 24 hours

Sources & evidence

ORD record
ord-7576ca553dd84dd78bf29cd51e2e8387
Source dataset
uspto-grants-2000_09
Patent number
US06121268

Reaction notes

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