Benzaldehyde → HCID 244688, compound

HRID 1418528Notes

Reaction equation

HRID 1418528 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.[OH-].[Ba+2].[OH-].C(O)C>Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:8](=[O:10])[CH:9]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 702EthanolHCID 84873-HydroxyacetophenoneHCID 17749100Barium hydroxide, monohydrate

Product 1

HCID 244688HCID 244688, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a 250 ml round bottom flask equipped with a magnetic stirrer and reflux condensor, 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 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 mls of 1N aqueous hydrochloric acid, and another solid was observed to precipitate from solution. The solid was collected by vacuum filtration, and washed with 100 mls of water, then 100 mls of hexane and dried in vacuo at 40° C. for 24 hours. 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 condensor
  3. temperatureThe reaction was refluxed for a total of 2.5 hours
  4. temperatureUpon cooling
  5. customto precipitate from solution
  6. filtrationThe solid was collected by vacuum filtration
  7. washwashed with 100 mls of water
  8. dry with material100 mls of hexane and dried in vacuo at 40° C. for 24 hours

Sources & evidence

ORD record
ord-1f659f2083fc4eb4a8439ce00796af51
Source dataset
uspto-grants-1999_03
Patent number
US05883125

Reaction notes

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