Sodium Iodide → HCID 12232689, compound

HRID 1658844Notes

Reaction equation

HRID 1658844 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH2:11][S:12]([CH3:15])(=[O:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[I-].[Na+]>O.CC(C)=O>[CH2:22]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 12232679HCID 12232679, compound

Product 1

HCID 12232689HCID 12232689, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 14.0 g. of 4'-hydroxy-3'-methylsulfonylmethylacetophenone, 9.3 g. of potassium carbonate, 7.8 ml. of benzyl chloride and a catalytic amount of sodium iodide in 250 ml. of acetone and 250 ml. of water is refluxed with stirring for 16 hours. The acetone is removed and the aqueous phase is extracted with chloroform, washed with water, dried and evaporated to yield an oil which is recrystallized in 2-propanol to give crystalline 4'-benzyloxy-3'methylsulfonylmethylacetophenone, m.p. 94°-97° C.

Workup

  1. additionA mixture of 14.0 g
  2. customThe acetone is removed
  3. extractionthe aqueous phase is extracted with chloroform
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customto yield an oil which
  8. customis recrystallized in 2-propanol

Sources & evidence

ORD record
ord-2407ae658ef54136ac6e92a24af04f56
Source dataset
uspto-grants-1976_06
Patent number
US03966770

Reaction notes

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