Dimethylformamide → 1,1'-[Sulfanediylbis(methylene-4,1-phenylene)]bis(2,2-dimethylpropan-1-one)

HRID 2398316Notes

Reaction equation

HRID 2398316 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:5][CH:4]=1.CN(C)[CH:17]=[O:18].O.O.O.O.O.O.O.O.O.[S-2:29].[Na+].[Na+]>O>[S:29]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:17](=[O:18])[C:10]([CH3:12])([CH3:11])[CH3:9])=[CH:7][CH:8]=1)[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 73972Sodium sulfide nonahydrateHCID 128310071-[4-(Bromomethyl)phenyl]-2,2-dimethylpropan-1-one

Product 1

HCID 681255451,1'-[Sulfanediylbis(methylene-4,1-phenylene)]bis(2,2-dimethylpropan-1-one)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 20.0 g. (0.078 mole) of α-bromo-p-pivaloyl toluene in 40 ml. dimethylformamide is warmed to 50° C. and treated dropwise with 9.4 g. (0.0392 mole) of sodium sulfide nonahydrate in 11 ml. water for about 15 minutes. The resulting solution is refluxed for 18 hours, cooled and poured onto 1 liter of ice/water. The aqueous solution is extracted twice with ether and the ether washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated. The residue is recrystallized from methanol to give 4',4'"-(thiodimethylene) bis(pivalophenone); m.p. 64°-65° C.

Workup

  1. additiontreated dropwise with 9.4 g
  2. temperatureThe resulting solution is refluxed for 18 hours
  3. temperaturecooled
  4. extractionThe aqueous solution is extracted twice with ether
  5. washthe ether washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-393483b604ed4e0885c3af10e1205e81
Source dataset
uspto-grants-1977_05
Patent number
US04024283

Reaction notes

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