2-Methyl-2-butene → 2,4,6,7-Tetramethyl-5-nitrodihydrobenzofuran-2-carboxylic acid

HRID 1987776Notes

Reaction equation

HRID 1987776 reaction equation
[CH3:1][C:2]1([CH:17]=[O:18])[CH2:6][CH:5]2[CH:7]([CH3:16])[C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:12])[C:10]([CH3:11])=[C:4]2[O:3]1.CC(=CC)C.Cl([O-])=[O:25].[Na+].[Na].[H][H]>C(O)(C)(C)C.O>[CH3:1][C:2]1([C:17]([OH:25])=[O:18])[CH2:6][CH:5]2[CH:7]([CH3:16])[C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:12])[C:10]([CH3:11])=[C:4]2[O:3]1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 866073542,4,6,7-Tetramethyl-5-nitrodihydrobenzofuran-2-aldehydeHCID 178506446HCID 178506446, compound

Product 1

HCID 688444542,4,6,7-Tetramethyl-5-nitrodihydrobenzofuran-2-carboxylic acidYield 47.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

2.39 g of 2,4,6,7-tetramethyl-5-nitrodihydrobenzofuran-2-aldehyde and 31 g of 2-methyl-2-butene were dissolved in 190 ml of t-butanol and a solution prepared by dissolving 7.77 g of sodium chlorite and 10.1 g of sodium dihydrogen phospahte dehydrate in 78 ml of water was added dropwise under ice cooling, followed by stirring at room temperature for 2 hours. After 2-methyl-2-butene and t-butanol were distilled off under reduced pressure, water was added and the reaction solution was extracted with ether. The solution was washed with saturated saline and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure and the residue was crystallized from ether-hexane to obtain 1.20 g of the objective product.

Workup

  1. customa solution prepared
  2. additionwas added dropwise under ice cooling
  3. distillationAfter 2-methyl-2-butene and t-butanol were distilled off under reduced pressure, water
  4. additionwas added
  5. extractionthe reaction solution was extracted with ether
  6. washThe solution was washed with saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe residue was crystallized from ether-hexane

Sources & evidence

ORD record
ord-7095fec11cb34b9b85c6c27de258702d
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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