p-Toluenesulfonic acid monohydrate → HCID 10679822, compound

HRID 1741325Notes

Reaction equation

HRID 1741325 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCCCC1[O:19][CH2:20][CH2:21][O:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33]>CO>[OH:19][CH2:20][CH2:21][O:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21834061HCID 21834061, compound

Product 1

HCID 10679822HCID 10679822, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.56 g of p-toluenesulfonic acid monohydrate was added to a solution of 8.62 g of N-[2-(tetrahydropyran-2-yloxy)ethoxy]phthalimide [prepared as described in step (a) above] in 86 ml of methanol, and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and then the resulting residue was dissolved in a mixture of ethyl acetate and water and neutralyzed with sodium hydrogen carbonate. The ethyl acetate layer was separated and-dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, giving the title compound as a crystalline powder. This was washed with diisopropyl ether to give 4.10 g of the pure compound, melting at 82-85° C.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. dissolutionthe resulting residue was dissolved in a mixture of ethyl acetate and water and neutralyzed with sodium hydrogen carbonate
  3. customThe ethyl acetate layer was separated
  4. dry with material-dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-47ca880867f54af08135d830ca041894
Source dataset
uspto-grants-1999_10
Patent number
US05972959

Reaction notes

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