Hydrochloric Acid → 2-(2-Acetamido-3-phenoxyphenyl)acetic acid

HRID 2418376Notes

Reaction equation

HRID 2418376 reaction equation
[C:1]([NH:4][C:5]1[C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:18][C:19]([O:21]CC)=[O:20])(=[O:3])[CH3:2].[OH-].[K+].CO.Cl>C(=O)(O)[O-].[Na+]>[C:1]([NH:4][C:5]1[C:10]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:18][C:19]([OH:21])=[O:20])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 20446298Ethyl 2-(2-acetamido-3-phenoxyphenyl)acetate

Product 1

HCID 204462492-(2-Acetamido-3-phenoxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of ethyl 2-(2-acetamido-3-phenoxyphenyl)acetate (3.65 g.), potassium hydroxide (1.3 g.) and methanol (50 ml.) was stirred for 4 hours at ambient temperature and then for an hour at 40° C. Methanol was distilled off from the reaction mixture under reduced pressure and the residue was dissolved in water. The solution was washed with diethyl ether, adjusted to pH 1.0 with 5% sulfuric acid and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then evaporated. The residue was recrystallized from a mixture of ethanol and n-hexane to give white needles of the captioned compound (3.1 g.). mp 155° to 156° C. Thus obtained product was dissolved in an aqueous solution of sodium bicarbonate and the solution was adjusted to pH 1.0 with 10% hydrochloric acid. The precipitates were collected by filtration and dried to give the pure compound (2.5 g.), mp 155° to 156° C.

Workup

  1. waitfor an hour at 40° C
  2. distillationMethanol was distilled off from the reaction mixture under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. washThe solution was washed with diethyl ether
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue was recrystallized from a mixture of ethanol and n-hexane
  10. customto give white needles of the captioned compound (3.1 g.)
  11. filtrationThe precipitates were collected by filtration
  12. customdried
  13. customto give the pure compound (2.5 g.), mp 155° to 156° C.

Sources & evidence

ORD record
ord-4033499f55f64f8a985859cfe8a1dd33
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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