Hydroxyphenylacetic acid → [p-(p-Cyanophenoxy)phenyl]acetic Acid

HRID 1863266Notes

Reaction equation

HRID 1863266 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.F[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C([O-])(O)=O.[Na+]>CN(C)C(=O)C>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=2)=[CH:14][CH:15]=1)#[N:18]

Participants

6

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 12531840[p-(p-Cyanophenoxy)phenyl]acetic Acid

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 15.2 g of p-hydroxyphenylacetic acid and 12.1 g of p-fluorobenzonitrile in 125 ml of N,N-dimethylacetamide is added, with vigorous stirring, 27.6 g of anhydrous potassium carbonate. The mixture is heated at 155°-160° C. under an Argon atmosphere with rapid stirring for 4 hours. After cooling to room temperature the mixture is poured into 300 ml of saturated NaHCO3. The mixture is extracted with two 100 ml portions of ether. The aqueous layer is acidified with 50 ml of concentrated HCl. The product is filtered washed with water (ca 500 ml) and dried to give a white solid mp 125.5°-127.5° C. A portion is recrystallized from 7:3 methanol-water (10 ml) to give white needles, mp 126.5°-128.5° C.

Workup

  1. temperatureThe mixture is heated at 155°-160° C. under an Argon atmosphere
  2. extractionThe mixture is extracted with two 100 ml portions of ether
  3. filtrationThe product is filtered
  4. washwashed with water (ca 500 ml)
  5. customdried

Sources & evidence

ORD record
ord-8219ffaa91174214a8a6a06657e7639f
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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