Benzaldehyde → T5637827

HRID 331259Notes

Reaction equation

HRID 331259 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCO>[OH:3][C:4]1[CH:5]=[C:6]([C:10](=[O:12])/[CH:11]=[CH:13]/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 84873-HydroxyacetophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 5356382T5637827Yield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

A 250 mL round-bottomed flask was charged sequentially aq. NaOH solution (NaOH 7.1 g/H2O 50 mL) and EtOH (40 mL). The solution was maintained below 10° C. in an ice bath. 1-(3-hydroxyphenyl)ethanone (20.0 g, 147 mmol) was added and stirred for 30 min at 10° C. To the resulting mixture was then added benzaldehyde (15 mL, 1.0 eq). After being stirred for additional 1 h at 10° C., the reaction mixture was stirred at room temperature for further 26 h. The solution was concentrated by rotary evaporation under reduced pressure. The residue was dissolved in EtOAc. The organic layer was washed with 3N HCl and H2O, dried over MgSO4, and concentrated in vacuo to obtain the desired product (32.5 g, 98%).

Workup

  1. temperatureThe solution was maintained below 10° C. in an ice bath
  2. stirringAfter being stirred for additional 1 h at 10° C.
  3. stirringthe reaction mixture was stirred at room temperature for further 26 h
  4. concentrationThe solution was concentrated by rotary evaporation under reduced pressure
  5. dissolutionThe residue was dissolved in EtOAc
  6. washThe organic layer was washed with 3N HCl and H2O
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b29e8f2f974d49dc81c4aea49cd65a8c
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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