Hydroquinone → Propane, 1,3-bis(ethenylsulfonyl)-

HRID 258787Notes

Reaction equation

HRID 258787 reaction equation
Cl[CH2:2][CH2:3][S:4]([CH2:7][CH2:8][CH2:9][S:10]([CH2:13][CH2:14]Cl)(=[O:12])=[O:11])(=[O:6])=[O:5].C1(C=CC(O)=CC=1)O.C(N(CC)CC)C>C(OCC)(=O)C>[CH:13]([S:10]([CH2:9][CH2:8][CH2:7][S:4]([CH:3]=[CH2:2])(=[O:6])=[O:5])(=[O:12])=[O:11])=[CH2:14]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 8471TriethylamineHCID 21424250HCID 21424250, compound

Product 1

HCID 5072300Propane, 1,3-bis(ethenylsulfonyl)-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

1,3-Bis(2-chloroethylsulfonyl)propane (74.5 g., 0.249 mole) was suspended in 2,300 ml. of ethyl acetate containing 0.12 g. hydroquinone. Triethylamine (50.7 g., 0.50 mole) was dropped in with stirring, within 10 minutes at 25° C. The resulting mixture was stirred at 25° C. for 20 hours. The amine salt was filtered off and the ethyl acetate solution evaporated at 30° C. The tan-colored solid was washed with water, then recrystallized from ethanol; yield 32.8 g. (59 percent); m.p. 60°-63° C.

Workup

  1. stirringThe resulting mixture was stirred at 25° C. for 20 hours
  2. filtrationThe amine salt was filtered off
  3. customthe ethyl acetate solution evaporated at 30° C
  4. washThe tan-colored solid was washed with water
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-05f74795aa924f489d8c2fbce9c07bfb
Source dataset
uspto-grants-1977_07
Patent number
USRE029305

Reaction notes

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