Water → N-(1-(4-chloromethylphenyl)ethyl)acetamide

HRID 1282088Notes

Reaction equation

HRID 1282088 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9](O)[CH3:10])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[OH2:17].[C:18](#[N:20])[CH3:19]>>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:20][C:18](=[O:17])[CH3:19])[CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 12600511HCID 12600511, compound

Product 1

HCID 18423033N-(1-(4-chloromethylphenyl)ethyl)acetamide

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(4-chloromethylphenyl)ethanol (17 g) in acetonitrile (102 ml) was added dropwise conc. sulfuric acid (5.7 ml) under ice-cooling. The mixture was stirred at 0° C. for 3.5 hr and left standing overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with an aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a white solid. This solid was recrystallized from ethyl acetate-isopropyl ether to give the title compound (17 g) as white crystals.

Workup

  1. temperaturecooling
  2. waitleft
  3. waitstanding overnight
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with an aqueous sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customto give a white solid
  9. customThis solid was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-97417c8f4b424dce9b8d539cf5d86f52
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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