Water → 2,3-Dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate

HRID 27641Notes

Reaction equation

HRID 27641 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:15]S(=O)O[CH2:12][C:11]([CH3:18])([CH3:17])[C:10]=2[CH:19]=1)(=[O:4])=[O:3].[Cl-].[Na+].O>CN(C)C=O>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:15][CH2:12][C:11]([CH3:18])([CH3:17])[C:10]=2[CH:19]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 233412714,5-Dihydro-5,5-dimethyl-2-oxido-1,3,2-benzodioxathiepin-7-yl methanesulphonate

Product 1

HCID 233412912,3-Dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonateYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,5-dihydro-5,5-dimethyl-2-oxido-1,3,2-benzodioxathiepin-7-yl methanesulphonate (24 parts) (from Example 20) and sodium chloride (1 part) in dimethyl formamide (400 parts) was boiled under reflux for 3 hours. The mixture was then added to water and the product extracted with ether to give 2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulphonate (16 parts, 84% yield), identical with the product of Example 37(a) above.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionthe product extracted with ether

Sources & evidence

ORD record
ord-f45d7e3e3172440680c1aa4c0a000400
Source dataset
uspto-grants-1980_09
Patent number
US04222767

Reaction notes

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