Benzenesulfonyl chloride → Butylvinyl ether benzenesulfonate

HRID 368803

Reaction equation

HRID 368803 reaction equation
CC(C)([O-:4])C.[Na+].O[CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH:13]=[CH2:14].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[C:15]1([S:21]([OH:23])(=[O:4])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:11]([O:12][CH:13]=[CH2:14])[CH2:10][CH2:9][CH3:8]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 873291,4-Butanediol monovinyl etherHCID 23676156Sodium t-butoxide

Product 1

HCID 86755948Butylvinyl ether benzenesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

Into a 3 L flask equipped with a mechanical stirrer and N2 purge was added 1000 g of tetrahydrofuran and 220.7 g (2.3 mol) of sodium t-butoxide. Hydroxybutyvinyl ether (236 g, 2.03 mol) was added dropwise at a rate to maintain the temperature at ≤40° C. This reaction mass was cooled to -40° C. A solution of benzenesulfonyl chloride (353 g, 2 mol) in 300 g of tetrahydrofuran was added dropwise at a rate to maintain the reaction temperature at ≤-20° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature to obtain the butylvinyl ether benzenesulfonate, ##STR8##

Workup

  1. customInto a 3 L flask equipped with a mechanical stirrer
  2. customN2 purge
  3. temperatureto maintain the temperature at ≤40° C
  4. temperatureto maintain the reaction temperature at ≤-20° C
  5. additionAfter the addition
  6. temperatureto warm to room temperature

Sources & evidence

ORD record
ord-75b3272298c14e71a4329f759da616bb
Source dataset
uspto-grants-2000_10
Patent number
US06133472

Linked notes

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