Acetic Anhydride → 3-Hydroxyacetanilide

HRID 846500Notes

Reaction equation

HRID 846500 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>O>[CH3:10][C:9]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=1)=[O:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 115683-Aminophenol

Product 1

HCID 121243-HydroxyacetanilideYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In the manner of Example 2, Step A, the reaction of 66.0 g (0.60 mole) of 3-aminophenol and 77.8 g (0.76 mole) of acetic anhydride in 180 mL of water gave 81.0 g of 3-hydroxyacetanilide as a solid, mp 144°-146.C. The reaction was repeated to obtain an additional quantity of product.

Sources & evidence

ORD record
ord-d5a1865025ff494bbe3fa5fc2f10d366
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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