Sulfuric Acid → N-(1,1-Dimethyl-2-phenylethyl)acetamide

HRID 2172705Notes

Reaction equation

HRID 2172705 reaction equation
[CH3:1][C:2](O)([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12](#[N:14])[CH3:13].S(=O)(=O)(O)[OH:16].[OH-].[Na+]>C(O)(=O)C>[CH3:1][C:2]([NH:14][C:12](=[O:16])[CH3:13])([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 75312-Methyl-1-phenyl-2-propanolHCID 14798Sodium Hydroxide

Product 1

HCID 266405N-(1,1-Dimethyl-2-phenylethyl)acetamideYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 2-methyl-1-phenyl-2-propanol (1.5 g, 10 mmol) and acetonitrile (3 mL) in acetic acid (15 mL) was added concentrated sulfuric acid (3 mL) dropwise at room temperature. The mixture was stirred at 65° C. for 3 hours and then poured into ice-water (ca. 200 mL). The aqueous solution was basified with saturated aqueous sodium hydroxide until pH>11. The suspension was stirred for further 0.5 hour, and then the precipitated solid was filtered and washed with water. The white solid was air-dried to give N-(2-methyl-1-phenylpropan-2-yl)acetamide (1.5 g, 78% yield), which was used for the next step without further purification.

Workup

  1. stirringThe suspension was stirred for further 0.5 hour
  2. filtrationthe precipitated solid was filtered
  3. washwashed with water
  4. customThe white solid was air-dried

Sources & evidence

ORD record
ord-120d39883f414e7f9cafd6fece8dff30
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

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