Methanesulfonic Acid → HCID 12094550, compound

HRID 2119688Notes

Reaction equation

HRID 2119688 reaction equation
CS(O)(=O)=O.[C:6]([C:10]1[C:15]2[CH2:16][CH:17]([CH3:19])[O:18][C:14]=2[CH:13]=[CH:12][C:11]=1[OH:20])([CH3:9])([CH3:8])[CH3:7]>C(O)(C)(C)C.C(Cl)(Cl)Cl>[C:6]([C:10]1[C:15]2[CH2:16][CH:17]([CH3:19])[O:18][C:14]=2[C:13]([C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:12][C:11]=1[OH:20])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 23442892HCID 23442892, compound

Product 1

HCID 12094550HCID 12094550, compoundYield 112.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

Under ice-cooling, 3 ml of methanesulfonic acid was added dropwise to a solution of 0.77 g of 4-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran in 1.5 g of t-butyl alcohol and 6 ml of chloroform. After stirring at 0° C. for 10 minutes, the mixture was poured into ice water 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 chloroform) to give 0.55 g of 4,7-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran as a white crystal (yield 57%).

Workup

  1. temperatureUnder ice-cooling
  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 chloroform)

Sources & evidence

ORD record
ord-c04a089b47d14a479af7e3a3a613e773
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

Loading…