p-Toluenesulfonic acid monohydrate → HCID 10679822, compound

HRID 1956932Notes

Reaction equation

HRID 1956932 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 materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-5cc3f372e14d4091939754602b4902d0
Source dataset
uspto-grants-1998_07
Patent number
US05780490

Reaction notes

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