Acetic Anhydride → HCID 14910078, compound

HRID 972793Notes

Reaction equation

HRID 972793 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 (2.4 g, 0.0115 mole) until the solid dissolved. Acetic anhydride (3.0 ml) was quickly added to the solution (pH 10) with vigorous stirring at 10°-15°, after which the pH was in the range 4-5, and stirring was continued for a further hour. 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 (2.2 g, 76%, m.p. 205°-206°).

Workup

  1. dissolutiondissolved
  2. stirringstirring
  3. waitwas continued for a further hour
  4. customThe precipitated solid was collected
  5. washwashed with water
  6. customa second crop was obtained by evaporation of the filtrate and addition of water to the residue
  7. customThe combined solids were recrystallised from ethanol

Sources & evidence

ORD record
ord-9bb9cea08bb44b968495dc2664f53708
Source dataset
uspto-grants-1977_10
Patent number
US04053601

Reaction notes

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