Isopropanol → HCID 13603546, compound

HRID 2412816Notes

Reaction equation

HRID 2412816 reaction equation
CC(O)C.[CH3:5][C:6]1([CH3:20])[CH2:10][C:9]2[CH:11]=[CH:12][C:13]([S:17]([O-:19])=[O:18])=[C:14]([O:15][CH3:16])[C:8]=2[O:7]1.[Li+].[Cl:22]N1C(=O)CCC1=O>O>[CH3:5][C:6]1([CH3:20])[CH2:10][C:9]2[CH:11]=[CH:12][C:13]([S:17]([Cl:22])(=[O:19])=[O:18])=[C:14]([O:15][CH3:16])[C:8]=2[O:7]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 31398ChlorosuccinimideHCID 23704281HCID 23704281, compound

Product 1

HCID 13603546HCID 13603546, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension composed of 100 ml of water and 100 ml of 2-propanol and containing 24.8 g of lithium 2,3-dihydro-2,2-dimethyl-7-methoxy-6-benzofuransulfinate is added portionwise 14.7 g of N-chlorosuccinimide. The reaction temperature is maintained at 15°-20° during the addition by occasional cooling with an ice-water bath. After addition is complete, the suspension is stirred at ambient temperature for one hour and then is diluted with water. The aqueous mixture is extracted twice with methylene chloride. The combined organic extractions are dried over sodium sulfate and then the solvent is evaporated under reduced pressure to afford crude 2,3-dihydro-2,2-dimethyl-7-methoxy-6-benzofuransulfonyl chloride.

Workup

  1. temperatureThe reaction temperature is maintained at 15°-20° during the addition
  2. temperatureby occasional cooling with an ice-water bath
  3. additionAfter addition
  4. extractionThe aqueous mixture is extracted twice with methylene chloride
  5. extractionThe combined organic extractions
  6. dry with materialare dried over sodium sulfate
  7. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-e1423816966a47e1894dd0da7d668f43
Source dataset
uspto-grants-1985_01
Patent number
US04494979

Reaction notes

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