4-Methylbenzaldehyde → HCID 5918629, compound

HRID 915181Notes

Reaction equation

HRID 915181 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH3:10][CH:11]([CH3:15])[C:12](=[O:14])[CH3:13].[OH-].[Ba+2].[OH-]>C(O)C>[CH3:10][CH:11]([CH3:15])[C:12](=[O:14])/[CH:13]=[CH:7]/[C:4]1[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 112513-Methyl-2-butanoneHCID 6093286Barium hydroxide

Product 1

HCID 5918629HCID 5918629, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of p-tolualdehyde (1 mL, 8.48 mmol), 3-methyl-2-butanone (1.81 mL, 16.96 mmol) and barium hydroxide (0.2 g, 1.17 mmol) in ethanol (4 mL) were mixed and the reaction mixture was heated at reflux for 1 hour. After cooling the solution was extracted with ethyl acetate. The organic layer was washed with water and brine, dried (Mg2SO4), filtered and evaporated to give 1.43 g of trans-4-methyl-1-p-tolyl-pent-1-en-3-one (90%) and used without further purification in the next step (step i). 1H NMR (300 MHz; CDCl3): 1.16 (d, J=7.2 Hz, 6 H), 2.35 (s, 3 H), 2.92 (m, 1 H), 6.79 (dd, J=16.0 Hz, 1 H), 7.19 (d, J=7.5 Hz, 1 H), 7.43 (d, J=8.1 Hz, 1 H), 7.28 (d, J=16.2 Hz, 1 H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperatureAfter cooling the solution
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried (Mg2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-c5d6ddd88bd74918b673716a2b67fbac
Source dataset
uspto-grants-2007_09
Patent number
US07265139B2

Reaction notes

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