Hydrochloric Acid → 4-Acetamido-3-(2-hydroxyethoxy)benzoic acid

HRID 1451083Notes

Reaction equation

HRID 1451083 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][C:6]=1[O:15][CH2:16][CH2:17][OH:18])(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(OCC)(=O)C>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[O:15][CH2:16][CH2:17][OH:18])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10491072Methyl 4-acetylamino-3-(2-hydroxyethoxy)benzoate

Product 1

HCID 5060834-Acetamido-3-(2-hydroxyethoxy)benzoic acidYield 34%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A sample of methyl 4-acetylamino-3-(2-hydroxyethoxy)benzoate (1.51 g, 0.0060 mol) was suspended in 1N NaOH (12.0 mL, 0.0119 mol). After stirring for 1 h, thin-layer chromatographic analysis (SiO2, ethyl acetate) showed disappearance of starting material along with appearance of a new lower-running spot (Rf =0.1) indicating the reaction was complete. The reaction mixture when neutralized with concentrated HCl formed a white precipitate. The material was collected by filtration, washed with water, and then dried in vacuo at acetone reflux to give 0.47 g (34%) of the title compound as a tan solid, mp 207.5°-208.5° C.

Workup

  1. customformed a white precipitate
  2. filtrationThe material was collected by filtration
  3. washwashed with water
  4. dry with materialdried in vacuo at acetone
  5. temperaturereflux

Sources & evidence

ORD record
ord-7541a270f96f4100ac56431eb5f2be92
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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