Water → O-acetyl-4-methacrylamidosalicylic acid

HRID 227199Notes

Reaction equation

HRID 227199 reaction equation
[C:1]([NH:6][C:7]1[CH:8]=[C:9]([OH:16])[C:10](=[CH:14][CH:15]=1)[C:11]([OH:13])=[O:12])(=[O:5])[C:2]([CH3:4])=[CH2:3].O.[C:18](OC(=O)C)(=[O:20])[CH3:19]>S(=O)(=O)(O)O>[C:18]([O:12][C:11](=[O:13])[C:10]1[C:9](=[CH:8][C:7]([NH:6][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[CH:15][CH:14]=1)[OH:16])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 125212724-Methacrylamidosalicylic acid

Product 1

HCID 86591029O-acetyl-4-methacrylamidosalicylic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
0 °C

Procedure

A few drops of concentrated sulfuric acid is added to a stirring solution of 35.0 g of 4-methacrylamidosalicylic acid (prepared according to Example 1) in 350 mL of acetic anhydride at 0° C. The solution is stirred for 60 minutes at 0° C. and then for an additional 6 hours at room temperature. The reaction mixture is then poured into 800 g of cold deionized water. The solid product precipitates from solution, and is collected by filtration. The product is then air dried at room temperature to afford A-4-MASA in quantitative yield.

Workup

  1. waitfor an additional 6 hours at room temperature
  2. additionThe reaction mixture is then poured into 800 g
  3. customThe solid product precipitates from solution
  4. filtrationis collected by filtration
  5. customair dried at room temperature
  6. customto afford A-4-MASA in quantitative yield

Sources & evidence

ORD record
ord-329e8b2265ee4308810cd5022d2b942e
Source dataset
uspto-grants-2009_07
Patent number
US07560032B2

Reaction notes

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