Sulfuric Acid → HCID 23109632, compound

HRID 968969Notes

Reaction equation

HRID 968969 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([CH3:13])(O)[CH3:11])[CH:5]=[CH:6][C:7]=1[CH3:8].S(=O)(=O)(O)O.[OH-:19].[Na+].[Cl:21][CH2:22][C:23]#[N:24]>C(O)(=O)C>[Cl:21][CH2:22][C:23]([NH:24][C:10]([CH3:13])([CH3:11])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([F:1])[CH:3]=1)=[O:19]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7856ChloroacetonitrileHCID 14798Sodium HydroxideHCID 23109551HCID 23109551, compound

Product 1

HCID 23109632HCID 23109632, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(3-Fluoro-4-methylphenyl)-2-methylpropan-2-ol (130.1 g) obtained in Step 5 was dissolved in chloroacetonitrile (139 ml) and acetic acid (115 ml), and concentrated sulfuric acid (33.4 ml) was added dropwise under ice-cooling. The mixture was stirred at room temperature for 2 hrs and 4N-aqueous sodium hydroxide solution (16 ml) was added dropwise under ice-cooling. The mixture was extracted twice with toluene and twice with ethyl acetate. The organic layer was washed twice with 10% brine and concentrated under reduced pressure to give the title compound (131.6 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionThe mixture was extracted twice with toluene and twice with ethyl acetate
  4. washThe organic layer was washed twice with 10% brine
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-259df542fe054a19a3d84ca77aeace25
Source dataset
uspto-grants-2007_12
Patent number
US07304174B2

Reaction notes

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