tert-Butanol → HCID 18687705, compound

HRID 1872867Notes

Reaction equation

HRID 1872867 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]2S[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)([CH3:4])([CH3:3])[CH3:2].[S:20]([O-:25])(O[O-])(=O)=[O:21].[K+].[K+].C([O-])(=O)C.[Na+].C(O)(C)(C)C>O>[C:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:20](=[O:25])(=[O:21])[C:11]3[C:16]([O:17][C:18]=2[CH:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 517045Sodium AcetateHCID 10313463Potassium peroxymonosulphateHCID 18687734HCID 18687734, compound

Product 1

HCID 18687705HCID 18687705, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 1.05 gm (3.85 mmole) of 3-tert-butoxyphenoxathiin, 3.53 gm (11.5 mmole) of potassium peroxymonosulfate compound [OXONE™] (Dupont), 1.14 gm (14 mmole) of sodium acetate, 20 mL of water, and 20 mL of tert-butanol was stirred overnight. The reaction was diluted with 50 mL of water and extracted with 3×75 mL of chloroform. The combined organic layers were then washed with 2×100 mL of water and concentrated in vacuo (water pump). The residue was then chromatographed on silica gel using methylene chloride to yield 0.89 gm of 3-tert-butoxyphenoxathiin 10,10-dioxide, m.p. 108-110°.

Workup

  1. extractionextracted with 3×75 mL of chloroform
  2. washThe combined organic layers were then washed with 2×100 mL of water
  3. concentrationconcentrated in vacuo (water pump)
  4. customThe residue was then chromatographed on silica gel

Sources & evidence

ORD record
ord-f4209b8180c04834bc064c37b957d6ad
Source dataset
uspto-grants-2000_08
Patent number
US06110961

Reaction notes

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