Sodium Thiosulfate → 5-Acetoxy-4,6-di-t-butyl-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran

HRID 1871493Notes

Reaction equation

HRID 1871493 reaction equation
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([OH:15])=[C:7]([CH2:16][C:17]([CH3:19])=[CH2:18])[C:6]=1[C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:32])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:9][C:8]2[O:15][C:17]([CH2:19][OH:32])([CH3:18])[CH2:16][C:7]=2[C:6]=1[C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 15485718HCID 15485718, compound

Product 1

HCID 154857195-Acetoxy-4,6-di-t-butyl-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuranYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 200 ml of chloroform was dissolved 10.0 g of 4-acetoxy-3,5-di-t-butyl-2-(2-methyl-2-propenyl)phenol synthesized in accordance with JP 6-206842 A/94, and 11.0 g of m-chloroperbenzoic acid was added thereto, followed by heating under reflux for one day. After cooling, a saturated aqueous solution of sodium thiosulfate was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (25% ethyl acetate in n-hexane) to give 7.3 g (yield: 70%) of 5-acetoxy-4,6-di-t-butyl-2-hydroxymethyl-2-methyl-2,3-dihydrobenzofuran (rotational isomer mixture) as a colorless oil.

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureunder reflux for one day
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with chloroform
  6. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (25% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-4deb1c1fcddd41a388f2558ed7b71bfd
Source dataset
uspto-grants-2000_08
Patent number
US06103753

Reaction notes

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