4-Hydroxybenzoic Acid → 4-(4-cyanophenoxy)benzoic acid

HRID 1824310Notes

Reaction equation

HRID 1824310 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.F[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].Cl>CC(N(C)C)=O>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([O:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)=[CH:13][CH:14]=1)#[N:17]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 21798064-(4-cyanophenoxy)benzoic acidYield 39%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 4-hydroxybenzoic acid (3.50 g, 25 mmol), 4-fluorobenzonitrile (3.00 g, 35 mmol), and powdered K2CO3 (6.80 g, 49 mmol) were heated in DMAC (50 mL) at 140° C. for 20 hours. The cooled mixture was then acidified with 1N HCl and extracted with EtOAc (3×50 mL). Concentration of the extracts in vacuo left a residue which was chromatographed over silica gel (5% MeOH/CHCl3) to provide 2.30 g (39%) of pure product. MS (FD+) 238.9

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. waitConcentration of the extracts in vacuo left a residue which
  3. customwas chromatographed over silica gel (5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-8ea639f58fb5497baf396304e9898926
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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