Acetyl chloride → N-((4-hydroxymethyl-2,6-dimethylphenyl)methyl)acetamide

HRID 1282063Notes

Reaction equation

HRID 1282063 reaction equation
[NH2:1][CH2:2][C:3]1[C:10]([CH3:11])=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[CH3:12].C(=O)([O-])[O-].[K+].[K+].[C:19](Cl)(=[O:21])[CH3:20]>C(OCC)(=O)C.O>[OH:8][CH2:7][C:6]1[CH:9]=[C:10]([CH3:11])[C:3]([CH2:2][NH:1][C:19](=[O:21])[CH3:20])=[C:4]([CH3:12])[CH:5]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 23383595[4-(Aminomethyl)-3,5-dimethylphenyl]methanol

Product 1

HCID 18423136N-((4-hydroxymethyl-2,6-dimethylphenyl)methyl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-aminomethyl-3,5-dimethylbenzyl alcohol (2.3 g) in ethyl acetate (70 ml) was added a solution of potassium carbonate (2.0 g) in water (35 ml). To this solution was added acetyl chloride (0.95 ml) under ice-cooling. This mixture was stirred at room temperature for 1 hr. The reaction mixture was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was recrystallized from methanol-ethyl acetate to give the title compound (2.0 g) as white crystals, m.p.=193.5-194.5° C.

Workup

  1. temperaturecooling
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-31a2246e1d0d43958bb8a8d963dcdb21
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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