Sodium Sulfite → HCID 66735956, compound

HRID 1009856Notes

Reaction equation

HRID 1009856 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[Br-:20].OOS([O-])=O.[K+].S([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.O.CC(C)=O>[CH2:1]([O:8][C:9]1[C:14]([Br:20])=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([CH3:18])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 24437Sodium SulfiteHCID 253881Sodium BromideHCID 890054HCID 890054, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 66735956HCID 66735956, compoundYield 97.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To an acetone solution (300 mL) of 1-[4-(benzyloxy)-2-methylphenyl]ethanone (20.9 g, 87.1 mmol) were added an aqueous solution (100 mL) of NaBr (9.86 g, 95.9 mmol), water (200 mL), and Oxone (registered trade mark, oxone-persulfuric acid chloride, from Aldrich) (59.0 g, 95.9 mmol), and the mixture was stirred 2.5 hours at room temperature. To the reaction solution cooled in ice were added an aqueous solution (50 mL) of sodium sulfite (20 g), subsequently water and ethyl acetate to separate an organic layer. The organic layer was washed with 20% aqueous solution of sodium sulfite and brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure to obtain a mixture (27.2 g) of 1-[4-(benzyloxy)-5-bromo-2-methylphenyl]ethanone and 1-[4-(benzyloxy)-3-bromo-2-methylphenyl]ethanone. To the mixture were added a 5% aqueous solution (300 mL, 255 mol) of sodium hypochlorite and an aqueous solution (10 mL) of potassium hydroxide (4.80 g, 85.3 mmol), stirred at 120° C. for an hour, cooled to room temperature, and precipitated insoluble matter was filtered. To this insoluble matter was added 2 M hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with 2 M hydrochloric acid and brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was washed with methanol to obtain the title compound (16.6 g, 59%, 2 steps) as a colorless powder.

Workup

  1. temperatureTo the reaction solution cooled in ice
  2. customto separate an organic layer
  3. washThe organic layer was washed with 20% aqueous solution of sodium sulfite and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7c5c6348fc624ef89429b440bd7fb7de
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

Loading…