Potassium Carbonate → [p-(p-Cyanophenoxy)phenyl]acetic Acid

HRID 1863316Notes

Reaction equation

HRID 1863316 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]CC)=[O:19])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C)C(=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([O:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:15][CH:16]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 28310Ethyl 4-hydroxyphenylacetateHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
158 °C

Procedure

A mixture of 17.4 g of p-fluorobenzonitrile, 31.0 g of ethyl p-hydroxyphenylacetate, 23.8 g of potassium carbonate and 175 ml of N,N-dimethylacetamide is heated at 158° C. for 18 hours. The mixture is cooled and poured into 300 ml of cold sodium bicarbonate solution. The mixture is extracted with ether and the ether extracts washed with two 200 ml portions of 2 N NaOH. The aqueous solutions are saturated with salt and extracted with ether. The alkaline aqueous layer is acidified with cold hydrochloric acid to give a solid which is filtered and washed with water to give tan crystals. Recrystallization by dissolving in 300 ml of methanol, adding 200 ml of water and chilling gives the product as yellow needles, mp 125°-127° C.

Workup

  1. temperatureThe mixture is cooled
  2. extractionThe mixture is extracted with ether
  3. washthe ether extracts washed with two 200 ml portions of 2 N NaOH
  4. extractionextracted with ether
  5. customto give a solid which
  6. filtrationis filtered
  7. washwashed with water
  8. customto give tan crystals
  9. customRecrystallization
  10. dissolutionby dissolving in 300 ml of methanol
  11. additionadding 200 ml of water
  12. temperaturechilling

Sources & evidence

ORD record
ord-d5c2257d116d42e2b153f06f4b331374
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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