Phenol → 4-Cyano-2-phenoxybenzaldehyde

HRID 343934Notes

Reaction equation

HRID 343934 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5](F)[CH:4]=1)#[N:2].[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 27831503-Fluoro-4-formylbenzonitrile

Product 1

HCID 219054244-Cyano-2-phenoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A stirred mixture of 4-cyano-2-fluorobenzaldehyde (2.23 g, 15 mmol), phenol (1.6 g, 17 mmol) and potassium carbonate (2.35 g, 17 mmol) in dried dimethylformamide (15 ml) was heated to 120° C. for 1 hour. After cooling, the mixture was diluted with water (50 ml) and extracted with diethyl ether (2×25 ml). The extracts were washed with 0.1M sodium hydroxide (2×50 ml), brine (50 ml), dried, filtered and evaporated to a yellow oil. Flash chromatography on silica, eluting with diethyl ether:hexane 1:1, gave 4-cyano-2-phenoxybenzaldehyde as a yellow oil that crystallised on standing.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether (2×25 ml)
  3. washThe extracts were washed with 0.1M sodium hydroxide (2×50 ml), brine (50 ml)
  4. customdried
  5. filtrationfiltered
  6. customevaporated to a yellow oil
  7. washFlash chromatography on silica, eluting with diethyl ether:hexane 1:1

Sources & evidence

ORD record
ord-b3c04f6578db463fb3842c370b4242ae
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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