Hydroquinone → Benzene, 1,4-bis(ethenesulfonylmethyl)-

HRID 258788

Reaction equation

HRID 258788 reaction equation
Cl[CH2:2][CH2:3][S:4]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][S:15]([CH2:18][CH2:19]Cl)(=[O:17])=[O:16])=[CH:10][CH:9]=1)(=[O:6])=[O:5].C(N(CC)CC)C.C1(C=CC(O)=CC=1)O>C(OCC)(=O)C.CN(C)C=O>[CH:18]([S:15]([CH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][S:4]([CH:3]=[CH2:2])(=[O:6])=[O:5])=[CH:9][CH:10]=1)(=[O:17])=[O:16])=[CH2:19]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 8471TriethylamineHCID 34820631,4-Bis{[(2-chloroethyl)sulfonyl]methyl}benzene

Product 1

HCID 4138103Benzene, 1,4-bis(ethenesulfonylmethyl)-

Reagents, catalysts & solvents 1

HCID 22989253N,N-dimethylformamide ethyl acetateSolvent

Procedure

A suspension consisting of 21.2 g. of α,α'-bis(2-chloroethylsulfonyl)-p-xylene (prepared from p-xylylene dichloride as in Example 1), 25 ml. of triethylamine, 0.05 g. of hydroquinone and 400 ml. of ethyl acetate-N,N-dimethylformamide (1:1 v./v.) were stirred at 25° C. for 20 hours and filtered. The filtrate was evaporated to 150 ml. volume, poured into water and the white solid isolated and recrystallized from methanol and ethyl acetate; m.p. 207°-212° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated to 150 ml
  3. additionvolume, poured into water
  4. customthe white solid isolated
  5. customrecrystallized from methanol and ethyl acetate

Sources & evidence

ORD record
ord-432cc3da6deb4923ac3cac606690fc4d
Source dataset
uspto-grants-1977_07
Patent number
USRE029305

Linked notes

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