Water → 2-[4-(Phenylacetamido)phenoxy]-2 methyl propionic acid

HRID 725017

Reaction equation

HRID 725017 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.O.[OH-].[Na+].[C:18]1([CH2:24][C:25](Cl)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1.[OH-].[Na+].CCOCC>[C:18]1([CH2:24][C:25]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[CH:13][CH:14]=2)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7679Phenylacetyl chlorideHCID 14798Sodium HydroxideHCID 27749582-(4-Aminophenoxy)-2-methylpropanoic acid

Product 1

HCID 98832742-[4-(Phenylacetamido)phenoxy]-2 methyl propionic acidYield 57.4%

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

FIG. 2C illustrates a general reaction scheme for preparing the Group I 2-[4-(arylacetamido)phenoxy]-2-methyl propionic acids. In accordance with the illustrated scheme, 1 g (0.005 mol) of 2-(4-aminophenoxy)-2-methyl propionic acid is dissolved with stirring in 10 ml of water containing 0.41 g (0.1 mol) of NaOH. To this solution, 0.79 g (0.005 mol) of phenyl acetyl chloride in 5 ml of tetrahydrofuran (THF) is gradually added over a period of about 15 minutes. After the addition is complete the pH of the reaction mixture should be alkaline (if not a few drops of 2N NaOH is added to assure alkalinity). The reaction mixture is continuously stirred for 1 hour. Thereafter, the THF is evaporated in vacuo, and the solution is then diluted with 5 ml water and acidified with concentrated hydrochloric acid. The product is extracted with ethyl ether (2×20 ml), washed with water (3×20 ml), and then dried over anhydrous MgSO4. Upon addition of petroleum ether to the ether solution, 0.9 g (56% yield) of the 2-[4-(phenylacetamido)phenoxy]-2-methyl propionic acid product precipitates as a pale brown solid, mp 173°-175° C.

Workup

  1. customa general reaction scheme
  2. additionAfter the addition
  3. additionis added
  4. customThereafter, the THF is evaporated in vacuo
  5. additionthe solution is then diluted with 5 ml water
  6. extractionThe product is extracted with ethyl ether (2×20 ml)
  7. washwashed with water (3×20 ml)
  8. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-1fb4fc2985204b089bfee8ccacbe8662
Source dataset
uspto-grants-1998_01
Patent number
US05705521

Linked notes

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