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

HRID 1452376Notes

Reaction equation

HRID 1452376 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-formylmethylanisole

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-95152c6d027c43f8b769824293943a48
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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