Benzenesulfinic acid, sodium salt → HCID 53905851, compound

HRID 1657549Notes

Reaction equation

HRID 1657549 reaction equation
[C:1]1([S:7]([O-:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].Cl[CH2:12][C:13]([CH3:20])=[CH:14][CH2:15][O:16][C:17](=[O:19])[CH3:18]>CN(C)C=O>[C:1]1([S:7]([CH2:12][C:13]([CH3:20])=[CH:14][CH2:15][O:16][C:17](=[O:19])[CH3:18])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium salt2×HCID 534009324-Chloro-3-methylbut-2-en-1-yl acetate

Product 1

HCID 53905851HCID 53905851, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of 24.2 g. of sodium benzenesulfinate in 150 ml. of dimethylformamide (DMF) was added 19.9 g. of 1-chloro-2-methyl-4-acetoxybut-2-ene in 50 ml. of DMF. The mixture was then heated to 60°C. for 4.5 hours. A second portion, 19.0 g. of sodium benzenesulfinate was added and the heating continued for 1.5 hours. The reaction mixture was poured into 1.5 l. of water and filtered to remove the solid which was dissolved in 500 ml. of ethyl acetate. This solution was washed with three 300 ml. portions of water and dried over magnesium sulfate. Evaporation of the solvent afforded 25.2 g. of crude sulfone acetate, m.p. 86°-92°C. Ethyl acetate extraction, washing and drying of the aqueous filtrate afforded an additional 6.07 g. of less pure product. Recrystallization of the main portion from ethyl acetate gave analytically pure 1-phenylsulfonyl-2-methyl-4-acetoxy-but-2-ene, m.p. 93°-94°C.

Workup

  1. additionTo a suspension of 24.2 g
  2. additionThe reaction mixture was poured into 1.5 l
  3. filtrationof water and filtered
  4. customto remove the solid which
  5. dissolutionwas dissolved in 500 ml
  6. washThis solution was washed with three 300 ml
  7. dry with materialportions of water and dried over magnesium sulfate
  8. customEvaporation of the solvent
  9. customafforded 25.2 g
  10. extractionEthyl acetate extraction
  11. washwashing
  12. customdrying of the aqueous filtrate
  13. customafforded an additional 6.07 g
  14. customRecrystallization of the main portion from ethyl acetate

Sources & evidence

ORD record
ord-757e150ad25147f9bd8390738ba9ec75
Source dataset
uspto-grants-1976_06
Patent number
US03960967

Reaction notes

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