3,5-Dinitrobenzoic acid → Ethene, 1,1'-[methylenebis(sulfonyl)]bis-
Reaction equation
Cl[CH2:2][CH2:3][S:4]([CH2:7][S:8]([CH2:11][CH2:12]Cl)(=[O:10])=[O:9])(=[O:6])=[O:5].[N+](C1C=C(C=C([N+]([O-])=O)C=1)C(O)=O)([O-])=O.C(N(CC)CC)C>CC(C)=O>[CH:11]([S:8]([CH2:7][S:4]([CH:3]=[CH2:2])(=[O:6])=[O:5])(=[O:10])=[O:9])=[CH2:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a well stirred solution of 53.84 g of bis-(2-chloroethylsulfonyl)methane in 300 ml of acetone containing 0.9 g of 3,5-dinitrobenzoic acid, was added dropwise at 20°-25° C. a solution of 40.48 g of triethylamine in 50 ml of acetone containing 0.15 g of 3,5-dinitrobenzoic acid. The reaction was stirred for 1 hour at 25° C. then cooled to -30° C. and filtered to remove triethylamine hydrochloride. The filtrate was evaporated to dryness on a rotary evaporator at 40° C. and water aspirator pressure. The residue was recrystallized from methanol containing 0.3 percent (wt/vol) of 3,5-dinitrobenzoic acid, to give 29.3 g (75 percent) of colorless crystalline bis(vinylsulfonyl)methane of m.p. 59°-61° C. This material readily dissolved in water to give a 2 percent by weight solution with no insoluble material present.
Workup
- temperaturethen cooled to -30° C.
- filtrationfiltered
- customto remove triethylamine hydrochloride
- customThe filtrate was evaporated to dryness on a rotary evaporator at 40° C.
- customThe residue was recrystallized from methanol containing 0.3 percent (wt/vol) of 3,5-dinitrobenzoic acid
Sources & evidence
- ORD record
- ord-d8ae1e997f0b48c9b0c6bb728723b597
- Source dataset
- uspto-grants-1979_10
- Patent number
- US04171976
Reaction notes
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