Chlorosulfonic acid → 2,2-Dimethyl-2,3-dihydro-1-benzofuran-5-sulfonyl chloride

HRID 1252344Notes

Reaction equation

HRID 1252344 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[O:3]1.[Cl:12][S:13](O)(=[O:15])=[O:14]>C(Cl)(Cl)Cl>[Cl:12][S:13]([C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([CH3:11])([CH3:1])[CH2:6][C:5]=2[CH:7]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 806402,3-Dihydro-2,2-dimethylbenzofuran

Product 1

HCID 156110382,2-Dimethyl-2,3-dihydro-1-benzofuran-5-sulfonyl chlorideYield 39.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 22.2 g (0.15 mole) of 2,3-dihydro-2,2-dimethylbenzofuran in 190 mL of chloroform was added dropwise 20 mL (0.3 mole) of chlorosulfonic acid. After complete addition, the reaction mixture was stirred at room temperature for two hours. The reaction mixture was poured into a separatory funnel with ice water and shaken. The organic layer was separated from the aqueous phase and dried over anhydrous magnesium sulfate. The dried organic phase was filtered and the filtrate was evaporated under reduced pressure to leave 14.5 g of 5-chlorosulfonyl-2,3-dihydro-2,2-dimethylbenzofuran as a solid (mp 75°-77° C.).

Workup

  1. additionAfter complete addition
  2. stirringshaken
  3. customThe organic layer was separated from the aqueous phase
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe dried organic phase was filtered
  6. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6e00d2ba500c4537afb8a7b2fba19e75
Source dataset
uspto-grants-1988_05
Patent number
US04743291

Reaction notes

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