Hydroxyphenylacetic acid → [4-(4-Nitrophenoxy)phenyl]acetic acid

HRID 1863264Notes

Reaction equation

HRID 1863264 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.[N+:12]([C:15]1[CH:20]=[CH:19][C:18](Cl)=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([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:17][CH:16]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 74741-Chloro-4-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 10858649[4-(4-Nitrophenoxy)phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 38 g of p-hydroxyphenylacetic acid, 39.4 g of 4-nitrochlorobenzene and 69 g of anhydrous potassium carbonate in 275 ml of N,N-dimethylacetamide is heated to 155°-160° C. over 2 hours, and maintained at that temperature, under Argon atmosphere for 4 hours with vigorous stirring. On cooling, an orange solid separated. A 1000 g solution of 5% NaHCO3 is added, resulting in a red brown solution. The solution is extracted with 4×100 ml of ether. The aqueous layer is acidified by the dropwise addition of 150 ml of concentrated HCl. A light yellow solid precipitates and is filtered and washed with 1500 ml of H2O to give the product, mp 132°-136° C. A sample is recrystallized from 19:1 methanol-water, to give the product, mp 135°-137° C.

Workup

  1. temperatureis heated to 155°-160° C. over 2 hours
  2. temperaturemaintained at that temperature, under Argon atmosphere for 4 hours with vigorous stirring
  3. temperatureOn cooling
  4. customan orange solid separated
  5. additionA 1000 g solution of 5% NaHCO3 is added
  6. customresulting in a red brown solution
  7. extractionThe solution is extracted with 4×100 ml of ether
  8. additionThe aqueous layer is acidified by the dropwise addition of 150 ml of concentrated HCl
  9. customA light yellow solid precipitates
  10. filtrationis filtered
  11. washwashed with 1500 ml of H2O
  12. customto give the product, mp 132°-136° C
  13. customA sample is recrystallized from 19:1 methanol-water
  14. customto give the product, mp 135°-137° C.

Sources & evidence

ORD record
ord-96609f439ea24cffb711e939ca7ef36f
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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