HCID 11726907, compound → 5-Acetoxy-4,6-di-tert-butyl-2,2-dimethyl-2,3-dihydrobenzofuran

HRID 1900500Notes

Reaction equation

HRID 1900500 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]CC(C)=C)=[CH:7][C:6]=1[C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:3])[CH3:2]>CN(C)C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]2[O:15][C:6]([CH3:20])([CH3:7])[CH2:5][C:7]=2[C:6]=1[C:20]([CH3:23])([CH3:21])[CH3:22])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 11726907HCID 11726907, compound

Product 1

HCID 109800835-Acetoxy-4,6-di-tert-butyl-2,2-dimethyl-2,3-dihydrobenzofuranYield 107.2%

Reagents, catalysts & solvents 1

HCID 949N,N-DimethylanilineSolvent

Procedure

4-Acetoxy-3,5-di-tert-butyl-l-(2-methyl-2-propenyloxy)benzene (2.22 g) was dissolved in N,N-dimethylaniline (8 ml) and the solution was refluxed under a nitrogen atmosphere for 36 h. After cooling to room temperature, the reaction solution was concentrated under reduced pressure and, after addition of 1N HCl (5 ml) and diethyl ether (10 ml), stirring was continued for 15 min. The organic layer was separated and the aqueous layer was subjected to extraction with diethyl ether. The combined extracts were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (5% ethyl acetate in n-hexane) to afford 5-acetoxy-4,6-di-tert-butyl-2,2-dimethyl-2,3-dihydrobenzofuran [1.19 g (yield, 54%)] as a white solid.

Workup

  1. temperaturethe solution was refluxed under a nitrogen atmosphere for 36 h
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionafter addition of 1N HCl (5 ml) and diethyl ether (10 ml)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was subjected to extraction with diethyl ether
  6. washThe combined extracts were washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe concentrate was purified by silica gel chromatography (5% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-3c332a10bd774c3db9dd8a1d8937b5aa
Source dataset
uspto-grants-1996_11
Patent number
US05574178

Reaction notes

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