Chloroacetamide → 2-(2-chloro-4-formylphenoxy)acetamide

HRID 1097341Notes

Reaction equation

HRID 1097341 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].CC(C)([O-])C.[K+].Cl[CH2:18][C:19]([NH2:21])=[O:20]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=[CH:8][C:9]=1[O:10][CH2:18][C:19]([NH2:21])=[O:20]

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 170223-Chloro-4-hydroxybenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 9777592-(2-chloro-4-formylphenoxy)acetamideYield 32.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-chloro-4-hydroxybenzaldehyde (10 g) in methanol (100 ml) was added 1.0 M potassium t-butoxide (64 ml). To the mixture was added 2-chloroacetamide (5.96 g) and the mixture heated under reflux overnight. The mixture was evaporated to the residue triturated with water (500 ml) and the solid collected to give the subtitle compound (4.4 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux overnight
  3. customThe mixture was evaporated to the residue
  4. customtriturated with water (500 ml)
  5. customthe solid collected

Sources & evidence

ORD record
ord-5479908ee79b4a109b4534da9ac86332
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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