Benzaldehyde → 2'-Methoxy-5'-methyl-2-benzylidenepropiophenone

HRID 4993Notes

Reaction equation

HRID 4993 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[C:10](=[O:13])[CH2:11][CH3:12].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[C:10](=[O:13])[C:11](=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:12]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 124318311-(2-Methoxy-5-methylphenyl)propan-1-one

Product 1

HCID 536369312'-Methoxy-5'-methyl-2-benzylidenepropiophenoneYield 101.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 140 g of 2'-methoxy-5'-methylpropiophenone, 83.4 g of benzaldehyde and 1.5 liters of ethanol was added 154 ml of 20%-sodium hydroxide aqueous solution under stirring. The reaction mixture was stirred overnight at room temperature, then 10%-hydrochloric acid was added to make the reaction mixture acidic, and extracted with benzene. The benzene extract was washed with water and an aqueous solution saturated with sodium chloride in this order, then dried to obtain 212 g of 2'-methoxy-5'-methyl-2-benzylidenepropiophenone. Yellow oily substance.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. extractionextracted with benzene
  3. extractionThe benzene extract
  4. washwas washed with water
  5. dry with materialan aqueous solution saturated with sodium chloride in this order, then dried

Sources & evidence

ORD record
ord-34bc9d0993fb467f9622700edbfc802b
Source dataset
uspto-grants-1993_09
Patent number
US05242919

Reaction notes

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