HCID 13267759, compound → HCID 13267760, compound

HRID 2413915Notes

Reaction equation

HRID 2413915 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:18])([CH3:17])[C:12]([O:14]CC)=[O:13])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>[OH-].[Na+].C(O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:18])([CH3:17])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 13267759HCID 13267759, compound

Product 1

HCID 13267760HCID 13267760, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

3.87 g of ethyl 2-(4-acetylaminophenyl)-2-methylpropionate was dissolved in a mixed solution of 16.6 ml of 2N-caustic soda solution and 30 ml of ethyl alcohol and the solution was stirred at 50° C. for 8 hours. After distilling off ethyl alcohol under reduced pressure, the aqueous layer was extracted with ether and unreacted materials were removed. After the aqueous layer was acidified with conc. hydrochloric acid, the formed crystals were collected by filtration, washed with water, and recrystallized from acetone-water to give 2.15 g of 2-(4-acetylaminophenyl)-2-methylpropionic acid (Yield: 62%). M.P. 169.7°-170.8° C.

Workup

  1. distillationAfter distilling off ethyl alcohol under reduced pressure
  2. extractionthe aqueous layer was extracted with ether and unreacted materials
  3. customwere removed
  4. filtrationthe formed crystals were collected by filtration
  5. washwashed with water
  6. customrecrystallized from acetone-water

Sources & evidence

ORD record
ord-9a33fb4726894c6a976fef1ab8c67a7c
Source dataset
uspto-grants-1988_01
Patent number
US04720506

Reaction notes

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