Acetyl chloride → Methyl 2-(4-acetamidomethylphenyl)-2-methylpropionate

HRID 1282118Notes

Reaction equation

HRID 1282118 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>O>[C:23]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18423094Methyl 2-(4-aminomethylphenyl)-2-methylpropionate

Product 1

HCID 18422995Methyl 2-(4-acetamidomethylphenyl)-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-(4-aminomethylphenyl)-2-methylpropionate (29.4 g) and triethylamine (23.8 ml) indichloroethane (300 ml) was added dropwise acetyl chloride (11.1 ml) at 5° C. over 30 min. The mixture was stirred at room temperature for 30 min. The reaction mixture was poured into water and the organic layer was separated. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=3:1, ethyl acetate) to give the title compound (23.47 g) as a pale-yellow oil.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=3:1, ethyl acetate)

Sources & evidence

ORD record
ord-db8e461a03de439da133f8be8db610b5
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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