Acetic Acid → HCID 20392585, compound

HRID 1704017Notes

Reaction equation

HRID 1704017 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)[CH3:2].[C:21](O)(=[O:23])[CH3:22].C(OC(=O)C)(=O)C>O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:21](=[O:23])[CH3:22])=[CH:17][CH:18]=2)=[CH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 20392571HCID 20392571, compound

Product 1

HCID 20392585HCID 20392585, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 6.8 g of ethyl[p-(p-aminophenoxy)phenyl]acetate, 7.5 ml of acetic acid, 5.4 ml of water and 8.75 g of crushed ice, maintained at 0°-5° C is added 2.8 g of acetic anhydride. The temperature immediately rises to 15° C. The stirring is continued for 2 hours, and extracted with two 50 ml portions of ether. The combined extracts are washed with 50 ml of H2O, 50 ml of saturated NaHCO3, 50 ml of saturated brine, and dried over MgSO4. Evaporation of the solvent affords the product as a tan solid, mp 95°-102° C. A portion is recrystallized from ethanol-hexane to give the product, mp 105°-107° C.

Workup

  1. temperaturemaintained at 0°-5° C
  2. customimmediately rises to 15° C
  3. extractionextracted with two 50 ml portions of ether
  4. washThe combined extracts are washed with 50 ml of H2O, 50 ml of saturated NaHCO3, 50 ml of saturated brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c117c32d64534f489cd4072a990403ec
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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