Water → HCID 12094373, compound

HRID 2119698Notes

Reaction equation

HRID 2119698 reaction equation
C([C:5]1[C:10]2[CH2:11][C:12]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[O:13][C:9]=2[CH:8]=[C:7]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:6]=1[OH:28])(C)(C)C.O>ClCCl.CS(O)(=O)=O>[C:24]([C:7]1[C:6]([OH:28])=[CH:5][C:10]2[CH2:11][C:12]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[O:13][C:9]=2[CH:8]=1)([CH3:25])([CH3:27])[CH3:26]

Participants

5

Reactant 2

HCID 962WaterHCID 98004724,6-Bis(1,1-dimethylethyl)-2,3-dihydro-2,2-dipentyl-5-benzofuranol

Product 1

HCID 12094373HCID 12094373, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To 1.03 g of 4,6-di-t-butyl-5-hydroxy-2,2-di-n-pentyl-2,3-dihydrobenzofuran synthesized according to JP No. 6-206842A/94 dissolved in 15 ml of dichloromethane was added 7 drops of methanesulfonic acid and the mixture was stirred at room temperature for a whole day and night. Then, the reaction mixture was combined with water and extracted with dichloromethane. 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 0.19 g of 6-t-butyl-5-hydroxy-2,2-di-n-pentyl-2,3-dihydrobenzofuran as a colorless oil (yield 22%).

Workup

  1. extractionextracted with dichloromethane
  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-84c1464ab85b475798d6dde42906ad57
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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