4-Toluenesulfonyl chloride → Chromanone

HRID 1045660Notes

Reaction equation

HRID 1045660 reaction equation
C1(C)C=CC(S(Cl)(=O)=[O:8])=CC=1.[O:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=NO)[CH2:14][CH2:13]1>N1C=CC=CC=1>[O:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:8])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 44866984H-1-Benzopyran-4-one, 2,3-dihydro-, oxime

Product 1

HCID 68110ChromanoneYield 97.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-Toluenesulfonyl chloride (52.5 g, 275 mmol) was added to a solution of chroman-4-one oxime (44.9 g, 275 mmol) in pyridine (275 ml) and the mixture was stirred for 12 hours at room temperature. Solvent was evaporated under reduced pressure and the residue was partitioned between water and chloroform. The organic layer was washed with 1N aqueous hydrochloric acid and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropylether, and dried to afford chroman-4-one O-p-toluenesulfoxime (85.1 g, 268 mmol, 97%) as white crystals.

Workup

  1. customSolvent was evaporated under reduced pressure
  2. customthe residue was partitioned between water and chloroform
  3. washThe organic layer was washed with 1N aqueous hydrochloric acid and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with diisopropylether
  7. customdried

Sources & evidence

ORD record
ord-98d3321bbac241f3afdeec629dd8fba2
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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