Hydrochloric Acid → Ethyl [p-(p-nitrophenoxy)phenyl]acetate

HRID 1704013Notes

Reaction equation

HRID 1704013 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.O.[CH2:23](O)[CH3:24]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH2:23][CH3:24])=[O:17])=[CH:11][CH:10]=2)=[CH:19][CH:20]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 962WaterHCID 10858649[4-(4-Nitrophenoxy)phenyl]acetic acid

Product 1

HCID 20392616Ethyl [p-(p-nitrophenoxy)phenyl]acetate

Procedure

A solution of 27.3 g of [p-(p-nitrophenoxy)phenyl]acetic acid in 270 ml of ethanol is cooled to 0° C and saturated with dry HCl gas over 3 1/2 hours. The resulting deep red solution is heated to reflux and maintained at reflux overnight. A yellow crystalline solid separates on cooling. The entire mixture is poured into 500 ml of water and extracted with three 200 ml portions of benzene. The combined extracts are washed with two 150 ml portions of water, two 150 ml portions of saturated NaHCO3, 150 ml of saturated brine, and dried over MgSO4. Evaporation of the solvent at reduced pressure affords an oil which yields yellow crystals from 50 ml of ethanol, mp 70.5°-73° C. Recrystallization from ethanol affords yellow prisms, mp 70.5°-73° C.

Workup

  1. temperatureThe resulting deep red solution is heated
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureat reflux overnight
  5. temperatureA yellow crystalline solid separates on cooling
  6. extractionextracted with three 200 ml portions of benzene
  7. washThe combined extracts are washed with two 150 ml portions of water, two 150 ml portions of saturated NaHCO3, 150 ml of saturated brine
  8. dry with materialdried over MgSO4
  9. customEvaporation of the solvent at reduced pressure
  10. customaffords an oil which
  11. customRecrystallization from ethanol
  12. customaffords yellow prisms, mp 70.5°-73° C.

Sources & evidence

ORD record
ord-3647ae35ff964b47860836e0402a0576
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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