Tetrahydrofuran → 4-Acetoxy-3,5-di-tert-butyl-2-formylmethylanisole

HRID 1376992Notes

Reaction equation

HRID 1376992 reaction equation
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([O:15][CH3:16])=[C:7](CC=C)[C:6]=1[C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].[O:37]1CC[CH2:39][CH2:38]1>O.[Os](=O)(=O)(=O)=O>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:12])([CH3:14])[CH3:13])=[CH:9][C:8]([O:15][CH3:16])=[C:7]([CH2:39][CH:38]=[O:37])[C:6]=1[C:20]([CH3:21])([CH3:22])[CH3:23])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 109360624-Acetoxy-3,5-di-tert-butyl-2-(2-propenyl)anisoleHCID 23667635Sodium periodate

Product 1

HCID 108817494-Acetoxy-3,5-di-tert-butyl-2-formylmethylanisoleYield 83%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

4-Acetoxy-3,5-di-tert-butyl-2-(2-propenyl)anisole (19 g) was dissolved in a 1:1 mixture (200 ml) of tetrahydrofuran and water. After adding osmium tetroxide (0.12 g) and sodium periodate (26.9 g), the mixture was stirred at room temperature for 48 h. After the end of the reaction, a saturated aqueous solution of sodium thiosulfate was added and the mixture was subjected to extraction with ethyl acetate and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (25% ethyl acetate in n-hexane) to afford 4-acetoxy-3,5-di-tert-butyl-2-formylmethylanisole [16 g (yield, 83%)].

Workup

  1. customAfter the end of the reaction
  2. extractionthe mixture was subjected to extraction with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel chromatography (25% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-9447f0aebf074493822c275833086cda
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Reaction notes

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