Ammonia → HCID 12898150, compound

HRID 648119Notes

Reaction equation

HRID 648119 reaction equation
N.O.[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[C:9]([C:17](=O)[C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][CH:19]=2)[CH:8]=1)([CH3:6])([CH3:5])[CH3:4]>C(O)C.[Zn].S([O-])([O-])(=O)=O.[Cu+2]>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[C:9]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:22][CH:23]=2)[CH:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 12898149HCID 12898149, compound

Product 1

HCID 12898150HCID 12898150, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24462Copper SulfateCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 25 ml of 30% aqueous ammonia and 12.5 ml of water was added to 17.5 g of active zinc powder. The mixture was heated at 80° C. with stirring. A saturated aqueous solution of copper sulfate (0.8 ml) was added, and then, a solution of 3.0 g of 4-t-butyl-2-(4-carboxymethylbenzoyl)phenylacetic acid in 25 ml of ethanol was added dropwise. The mixture was stirred at the same temperature for 30 hours. After the reaction, the reaction mixture was cooled, and the insoluble matter was separated by filtration. The filtrate was acidified with conc. hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The ethyl acetate was distilled off. Recrystallization of the residue from a mixture of ethyl acetate and n-hexane afforded 1.7 g of 4-t-butyl-2-(4-carboxymethylbenzyl)phenylacetic acid as colorless needle-like crystals having a melting point of 138° to 139° C.

Workup

  1. stirringThe mixture was stirred at the same temperature for 30 hours
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled
  4. customthe insoluble matter was separated by filtration
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialwith a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  8. distillationThe ethyl acetate was distilled off
  9. customRecrystallization of the residue
  10. additionfrom a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-29a2099083cc4e37a2373e95c3635685
Source dataset
uspto-grants-1983_10
Patent number
US04410716

Reaction notes

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