p-Toluenesulfonic acid monohydrate → HCID 12115482, compound

HRID 2373333Notes

Reaction equation

HRID 2373333 reaction equation
O[C:2]([C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11])([CH3:8])[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:8][CH:2]([C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11])[CH2:3][CH2:4][CH:5]([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12115481HCID 12115481, compound

Product 1

HCID 12115482HCID 12115482, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After 2.7 g (13.1 mols) of the 2-(1-hydroxy-1,4-dimethylpentyl)aniline obtained in Example 3-1 was diluted with toluene, p-toluenesulfonic acid monohydrate (225 mg) was added thereto, and the resulting mixture was dehydrated with refluxing over a period of 3 hours by the use of a Dean-Stark trap. The reaction mixture was diluted with ethyl acetate and then washed with an aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was dissolved in ethanol, followed by adding thereto 5% palladium-carbon (100 mg), and the resulting mixture was stirred under a hydrogen atmosphere at room temperature for 12 hours. The reaction mixture was filtered through Celite and the residue was concentrated under reduced pressure to obtain 2.2 g of 2-(1,4-dimethylpentyl)aniline.

Workup

  1. additionwas added
  2. temperaturewith refluxing over a period of 3 hours by the use of a Dean-Stark trap
  3. washwashed with an aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in ethanol
  7. additionby adding
  8. filtrationThe reaction mixture was filtered through Celite
  9. concentrationthe residue was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d751745395f14dd8b6977e9da34639a8
Source dataset
uspto-grants-2008_12
Patent number
US07459477B2

Reaction notes

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