Dimethylformamide → Styrene-4-sulfonyl chloride

HRID 1755498Notes

Reaction equation

HRID 1755498 reaction equation
C(C1C=C(O)C(=CC=1)O)(C)(C)C.S(Cl)([Cl:15])=O.CN(C)C=O.[CH2:22]=[CH:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O-:33])(=O)=[O:31])=[CH:26][CH:25]=1.[Na+]>O>[CH2:22]=[CH:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([Cl:15])(=[O:33])=[O:31])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 73814-tert-ButylcatecholHCID 24386Thionyl ChlorideHCID 3571582Sodium 4-styrenesulfonate

Product 1

HCID 9855777Styrene-4-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a reaction vessel fitted with a cooling pipe, a stirrer, a thermometer and a nitrogen feed pipe, 2.0 parts of 4-tert-butylcatechol, 565 parts of thionyl chloride and 400 parts of dehydrated N,N-dimethylformamide were fed, and then stirred under ice cooling. To the solution obtained, while this was kept at 0° C. or below, 150 parts of formula-(18) sodium p-styrenesulfonate was dividedly added thereto. After its addition, the reaction solution was stirred for 24 hours while keeping the liquid temperature. After the reaction was completed, the reaction solution was poured into 1,500 parts of water to carry out extraction with toluene, and the organic layer formed was washed with ion-exchanged water. This organic layer was then dried with sodium sulfuric anhydride, followed by evaporation of the solvent under reduced pressure to obtain 128 parts (quantitative) of formula-(19) p-styrenesulfonic acid chloride.

Workup

  1. customInto a reaction vessel fitted with a cooling pipe, a stirrer
  2. customTo the solution obtained
  3. customthis was kept at 0° C. or below
  4. additionAfter its addition
  5. stirringthe reaction solution was stirred for 24 hours
  6. extractionextraction with toluene
  7. customthe organic layer formed
  8. washwas washed with ion-exchanged water
  9. dry with materialThis organic layer was then dried with sodium sulfuric anhydride
  10. customfollowed by evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-039bb62f399045c8859fd16898d073dc
Source dataset
uspto-grants-2015_10
Patent number
US09170514B2

Reaction notes

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