Acetic Anhydride → N-(4-Chloro-3-hydroxyphenyl)acetamide

HRID 1604857Notes

Reaction equation

HRID 1604857 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[OH:9].[C:10](OC(=O)C)(=[O:12])[CH3:11]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:10]([CH3:11])=[O:12])=[CH:4][C:3]=1[OH:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 806765-Amino-2-chlorophenol

Product 1

HCID 14122483N-(4-Chloro-3-hydroxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

0.05 Mole (7.17 grams) of 2-chloro-5-aminophenol is dissolved in 21 cc of dioxane at 75°C. There is then added, with agitation, 0.05 mole (5.1 grams) of acetic anhydride. At the end of this addition, the reaction medium is maintained for 10 minutes at 70°C and then cooled. The raw product which has crystallized in then filtered and recrystallized in a hydroalcoholic medium. It exhibits a melting point of 212°C.

Workup

  1. additionAt the end of this addition
  2. temperaturecooled
  3. customThe raw product which has crystallized
  4. filtrationin then filtered
  5. customrecrystallized in a hydroalcoholic medium

Sources & evidence

ORD record
ord-e74abaf0848c4bfeba9368c6a280c642
Source dataset
uspto-grants-1976_04
Patent number
US03948596

Reaction notes

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