Sulfuric Acid → N-[2-Methyl-1-(naphthalen-2-yl)propan-2-yl]acetamide

HRID 1349440Notes

Reaction equation

HRID 1349440 reaction equation
[CH3:1][C:2](O)([CH3:14])[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1.[C:16](#[N:18])[CH3:17].S(=O)(=O)(O)[OH:20].[OH-].[Na+]>C(O)(=O)C>[CH3:1][C:2]([NH:18][C:16](=[O:20])[CH3:17])([CH3:14])[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 107744191-(2-Naphthyl)-2-methyl-2-propanol

Product 1

HCID 22382419N-[2-Methyl-1-(naphthalen-2-yl)propan-2-yl]acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 2-methyl-1-(naphtahlen-2-yl)-2-propanol (500 mg) obtained in Step 7 were added acetonitrile (0.5 ml) and acetic acid (0.5 ml) in this order. After ice-cooling the mixture, sulfuric acid (0.5 ml) was added dropwise. The mixture was stirred under ice-cooling for 20 min and poured into a 1N aqueous sodium hydroxide solution, and the mixture was extracted with diethyl ether. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to recrystallization from ethyl acetate-n-hexane to give the title compound (303 mg).

Workup

  1. additionwas added dropwise
  2. temperaturecooling for 20 min
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was subjected to recrystallization from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-a2c725a81d01455eb43c15df71c986da
Source dataset
uspto-grants-2007_05
Patent number
US07211685B2

Reaction notes

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