p-Toluenesulfonic acid → HCID 19047035, compound

HRID 1780592Notes

Reaction equation

HRID 1780592 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([C:8]2[S:9][CH2:10][C:11]([C:14]([F:17])([F:16])[F:15])(O)[N:12]=2)[CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:14]([F:15])([F:16])[F:17])[N:12]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 19047036HCID 19047036, compound

Product 1

HCID 19047035HCID 19047035, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The tertiary alcohol (3.9 g, 0.013 mol) obtained in Step C was refluxed for 3 h in toluene (60 mL) in the presence of a catalytic amount of p-toluenesulfonic acid (0.2 g). Azeotropic removal of water was achieved by employing a Dean-Starke trap. After cooling to room temperature, the toluene was removed under vacuum. The residue was taken up in ethyl acetate (200 mL) and washed with 10% aqueous sodium carbonate and brine (100 mL each). The dried (MgSO4) solution was concentrated to give 2.5 g (68% yield) of the title compound as white solid melting at 98°-104° C. 1H NMR (300 MHz, CDCl3) δ 7.91-7.94 (m,2H), 7.53 (s,1H), 7.43-7.46 (m,1H), 2.51 (s,3H).

Workup

  1. customAzeotropic removal of water
  2. customthe toluene was removed under vacuum
  3. washwashed with 10% aqueous sodium carbonate and brine (100 mL each)
  4. dry with materialThe dried (MgSO4) solution
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-e8f4aa7c6ebd40c489c8d248f2abc79b
Source dataset
uspto-grants-1997_05
Patent number
US05631206

Reaction notes

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