Methanol → 5'-Chloro-2'-hydroxy-P-acetotoluidide

HRID 1741546

Reaction equation

HRID 1741546 reaction equation
CO.[NH2:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([CH3:11])=[CH:6][C:5]=1[OH:12].[C:13](OC(=O)C)(=[O:15])[CH3:14]>O>[Cl:10][C:8]1[C:7]([CH3:11])=[CH:6][C:5]([OH:12])=[C:4]([NH:3][C:13](=[O:15])[CH3:14])[CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 1045242-Amino-4-chloro-5-methylphenol

Product 1

HCID 36474595'-Chloro-2'-hydroxy-P-acetotoluidideYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of methanol, there were added 1.0 g (6.4 mmol) of 2-amino-4-chloro-5-methylphenol and 0.71 g (7.0 mmol) of acetic anhydride and stirred at room temperature for 30 minutes. To this solution, there was added 60 ml of water. The crystals thus precipitated were filtered and recrystallized from methanol. Thus 0.89 g (4.5 mmol) of N-(5-chloro-2-hydroxy-4-methylphenyl)acetamide was obtained as pale brown crystals. The yield was 70%.

Workup

  1. customThe crystals thus precipitated
  2. filtrationwere filtered
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-6ea64157d7f44c07b91511244cb404d4
Source dataset
uspto-grants-1994_08
Patent number
US05334225

Linked notes

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