P-Cresol → 4-(4-Methylphenoxy)benzaldehyde

HRID 1063910Notes

Reaction equation

HRID 1063910 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([CH3:17])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:17][C:12]1[CH:11]=[CH:10][C:15]([O:16][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 2879P-CresolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 47392074-(4-Methylphenoxy)benzaldehydeYield 98.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a stirred solution of 4-fluorobenzaldehyde (24.1 g) and p-cresol (21 g) in N,N-dimethylformamide (400 ml) was added powdered potassium carbonate (26.8 g) and the reaction mixture was stirred at 150° C. for 7.5 hours. After cooling, the reaction mixture was poured into ice water (1.4 kg). The mixture was extracted with ethyl acetate (1 l), washed with water (1 l×3), brine (1 l), dried over anhydrous magnesium sulfate and concentrated in vacuo to give 4-(4-methylphenoxy)benzaldehyde (40.7 g) as a light yellow oil.

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with ethyl acetate (1 l)
  3. washwashed with water (1 l×3), brine (1 l)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f2f8ca36403404ab0b0463ddea22341
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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