1,4-Benzodioxan → 2,3-Dihydro-1,4-benzodioxine-6-sulfonyl chloride

HRID 962745Notes

Reaction equation

HRID 962745 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[Cl:11][S:12](O)(=[O:14])=[O:13]>C(Cl)(Cl)Cl>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([S:12]([Cl:11])(=[O:14])=[O:13])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 103011,4-BenzodioxanHCID 24638Chlorosulfonic acid

Product 1

HCID 27761692,3-Dihydro-1,4-benzodioxine-6-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 12 g of 1,4-benzodioxane in 40 mL of chloroform cooled to -10° C. under calcium sulfate drying tube was added dropwise over 15 min, 6 mL of chlorosulfonic acid. The mixture was allowed to warm to 20C over 15 min, poured onto 400 mL of ice and extracted into 1 L of chloroform. Drying over MgSO4 and concentration under reduced pressure gave 21.5 g of 1,4-benzodioxane-6-sulfonylchloride as a white crystalline solid.

Workup

  1. additionwas added dropwise over 15 min
  2. extractionextracted into 1 L of chloroform
  3. dry with materialDrying over MgSO4 and concentration under reduced pressure

Sources & evidence

ORD record
ord-b83c69ce1fe04904b0a46b7414f8303f
Source dataset
uspto-grants-1998_06
Patent number
US05760054

Reaction notes

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