P-Cresol → 2-(4-methylphenoxy)benzaldehyde

HRID 1795111Notes

Reaction equation

HRID 1795111 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:10]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([CH3:17])[CH:11]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CC(N(C)C)=O.O>[CH3:17][C:12]1[CH:11]=[CH:10][C:15]([O:16][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 2879P-CresolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 14748712-(4-methylphenoxy)benzaldehydeYield 50.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-fluorobenzaldehyde (3.54 g, 28.5 mmol) in DMA (20 mL) is added p-cresol (3.08 g, 28.5 mmol) and K2CO3 (4.72 g, 34.2 mmol), and the reaction mixture is heated to 150° C. for 12 h. Once complete, the reaction mixture is cooled to room temperature and diluted with water (100 mL) prior to being poured into a separatory funnel containing ethyl acetate (250 mL). The organic layer is separated, washed with brine (2×) and dried over sodium sulfate prior to concentration. The crude product is purified by column chromatography (5% ethyl acetate in hexanes) to afford 2-(4-methylphenoxy)-benzaldehyde (3.05 g, 50%) as a light yellow oil.

Workup

  1. temperatureOnce complete, the reaction mixture is cooled to room temperature
  2. additionto being poured into a separatory funnel
  3. customThe organic layer is separated
  4. washwashed with brine (2×)
  5. dry with materialdried over sodium sulfate
  6. concentrationto concentration
  7. customThe crude product is purified by column chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8143b97cb05f4423a740ee25dfd7c1ee
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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