Acetic Anhydride → HCID 14910078, compound

HRID 596691Notes

Reaction equation

HRID 596691 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:17])=[C:8]([CH:16]=1)[C:9]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10].[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[C:18]([NH:3][C:4]1[CH:5]=[CH:6][C:7]([OH:17])=[C:8]([CH:16]=1)[C:9]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 20309512HCID 20309512, compound

Product 1

HCID 14910078HCID 14910078, compoundYield 76%

Procedure

Sodium hydroxide solution (0.2 N) was added to 3-(5-amino-2-hydroxybenzoyl)propionic acid (2.4g) until all the solid had dissolved. Acetic anhydride (3.0 ml) was quickly added to the solution (pH 10) with vigorous stirring at 10°-15° C, after which the pH reading was in the range 4-5, and stirring was continued for a further 60 minutes. The precipitated solid was collected and washed with water and a second crop was obtained by evaporation of the filtrate and addition of water to the residue. The combined solids were recrystallised from ethanol to give 3-(5-acetamido-2-hydroxybenzoyl)propionic acid (2.2g, 76%), m.p. 205°-206° C.

Workup

  1. dissolutionhad dissolved
  2. stirringstirring
  3. customThe precipitated solid was collected
  4. washwashed with water
  5. customa second crop was obtained by evaporation of the filtrate and addition of water to the residue
  6. customThe combined solids were recrystallised from ethanol

Sources & evidence

ORD record
ord-293a3ba8b3f64f2fa3e6fda77591ba76
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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