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

HRID 345126Notes

Reaction equation

HRID 345126 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 lilers of ethanol was added 154 ml of 20%-sodium hydroxide aquecus 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-dc3924ed9db8405d846d05d51740b540
Source dataset
uspto-grants-1991_10
Patent number
US05055474

Reaction notes

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