Sodium Hydroxide → 4,7-Di-t-butyl-5-hydroxy-2,3-dihydrobenzofuran

HRID 2119683Notes

Reaction equation

HRID 2119683 reaction equation
[C:1]([C:5]1[C:10]2[CH2:11][CH2:12][O:13][C:9]=2[CH:8]=[CH:7][C:6]=1[OH:14])([CH3:4])([CH3:3])[CH3:2].CS([O-])(=O)=O.[OH-].[Na+]>C(O)(C)(C)C.C(Cl)(Cl)Cl>[C:1]([C:5]1[C:10]2[CH2:11][CH2:12][O:13][C:9]=2[C:8]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:7][C:6]=1[OH:14])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 85257MethanesulfonateHCID 144849574-Tert-butyl-2,3-dihydro-5-benzofuranol

Product 1

HCID 120945494,7-Di-t-butyl-5-hydroxy-2,3-dihydrobenzofuranYield 97%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

In a solution of 2.84 g of 4-t-butyl-5-hydroxy-2,3-dihydrobenzofuran [J. Org. Chem. 53, 4135 (1988)] in 10.0 g of t-butyl alcohol and 20 ml of chloroform was added dropwise 10 ml of methane sulfonate under ice-cooling. The mixture was stirred at 0° C. for 15 minutes, then poured into ice water. Then, the mixture was neutralized with a 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The extracted layers were washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane) to give 1.78 g of 4,7-di-t-butyl-5-hydroxy-2,3-dihydrobenzofuran as a white crystal (yield 48%).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extracted layers were washed with a saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (in n-hexane)

Sources & evidence

ORD record
ord-905699449f6b4a318863e6f8c0ec556c
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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