Sodium Carbonate → [(3-Ethyl-2-penten-1-yl)sulfonyl]benzene

HRID 1973509Notes

Reaction equation

HRID 1973509 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]1([S:13]([O-:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Na+].Br[CH2:18][CH:19]=[C:20]([CH2:23][CH3:24])[CH2:21][CH3:22]>CO>[CH2:21]([C:20]([CH2:23][CH3:24])=[CH:19][CH2:18][S:13]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:15])=[O:14])[CH3:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2723840Benzenesulfinic acid, sodium saltHCID 109650661-bromo-3-ethyl-2-pentene

Product 1

HCID 20336764[(3-Ethyl-2-penten-1-yl)sulfonyl]benzeneYield 80.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.85 gm of sodium carbonate and 18.5 gm of sodium phenyl sulfinate were introduced into 60 cc of methanol. Then 20 gm of 1-bromo-3-ethyl-2-pentene were added within the space of about 30 minutes at room temperature to the resulting suspension, which then was agitated for 1 hour and 30 minutes at room temperature. Then the reaction mixture was poured into ice-water and the organic phase was separated by decanting. The aqueous phase was extracted with ethyl ether and the ether extracts were combined with the principal organic solution. The solution thus obtained was dried over magnesium sulfate and the solvent was removed under reduced pressure to obtain 21.665 gm of (3-ethyl-2-pentenyl)-phenylsulfone. A sample of this product was rectified under reduced pressure and the boiling point was 125° C under 0.02 mm pressure of mercury and its refractive index nD23 = 1.530.

Workup

  1. customthe organic phase was separated
  2. customby decanting
  3. extractionThe aqueous phase was extracted with ethyl ether
  4. customThe solution thus obtained
  5. dry with materialwas dried over magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-956714c4738b4b5fad4304f839d1a466
Source dataset
uspto-grants-1976_12
Patent number
US03997586

Reaction notes

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