Methanesulfonic Acid → 6-tert-Butyl-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-ol

HRID 2119697Notes

Reaction equation

HRID 2119697 reaction equation
C([C:5]1[C:10]2[CH2:11][C:12]([CH3:15])([CH3:14])[O:13][C:9]=2[CH:8]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=1[OH:20])(C)(C)C.CS(O)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:16]([C:7]1[C:6]([OH:20])=[CH:5][C:10]2[CH2:11][C:12]([CH3:15])([CH3:14])[O:13][C:9]=2[CH:8]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 100620264,6-di-t-butyl-5-hydroxy-2,2-dimethyl-2,3-dihydrobenzofuran

Product 1

HCID 157375206-tert-Butyl-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-olYield 41%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 0.28 g of 4,6-di-t-butyl-5-hydroxy-2,2-dimethyl-2,3-dihydrobenzofuran synthesized according to JP 6-206842A/94 dissolved in 5 ml of chloroform was added 0.06 ml of methanesulfonic acid and the mixture was stirred at room temperature for 4 hours. Then, the reaction mixture was combined with a saturated aqueous sodium bicarbonate solution and extracted with chloroform. The extracted layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 10% ethyl acetate) to give 0.09 g of 6-t-butyl-5-hydroxy-2,2-dimethyl-2,3-dihydrobenzofuran as a white solid (yield 41%).

Workup

  1. extractionextracted with chloroform
  2. washThe extracted layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 10% ethyl acetate)

Sources & evidence

ORD record
ord-b5c9bd622faa462fbe29e2b0e1e6bc0c
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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