Phenol → 4-Phenoxybenzaldehyde

HRID 1178021Notes

Reaction equation

HRID 1178021 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[O:16]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 661394-PhenoxybenzaldehydeYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 4-fluorobenzaldehyde (5 g, 40.28 mmol) and phenol (3.8 g, 44.42 mmol) in DMF (50 mL) was added K2CO3 (11.13 g, 80.57 mmol) and the resulting mixture was stirred at 110° C. overnight. The mixture was filtered, the filtrate was diluted with cold water and the product was extracted with EtOAc. The organic layer was washed with 5% aqueous NaOH solution, saturated brine solution and dried over sodium sulphate. The organic layer was then concentrated under reduced pressure to afford 7.7 g (96.5% yield) of 4-phenoxy benzaldehyde as a pale brown oil. 1H NMR: (CDCl3) δ 9.9 (s, 1H), 7.8 (d, 2H), 7.4 (t, 2H), 7.2 (t, 1H), 7.0 (t, 4H).

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with cold water
  3. extractionthe product was extracted with EtOAc
  4. washThe organic layer was washed with 5% aqueous NaOH solution, saturated brine solution
  5. dry with materialdried over sodium sulphate
  6. concentrationThe organic layer was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-67bbeea5bc044bfaa42ec6cd724f56e6
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…