p-Toluenesulfonic acid → 4-Chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran

HRID 440652Notes

Reaction equation

HRID 440652 reaction equation
[Cl:1][C:2]1[C:3]([CH2:12][C:13]([CH3:15])=[CH2:14])=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[C:3]2[CH2:12][C:13]([CH3:15])([CH3:14])[O:11][C:4]=2[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22404731HCID 22404731, compound

Product 1

HCID 224047764-Chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuranYield 84.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 20.0 g (0.088 mole) of 3-chloro-2-(2-methyl-2-propen-1-yl)-6-nitrophenol and 0.35 g (0.002 mole) of p-toluenesulfonic acid in 100 mL of xylene was heated at reflux for approximately 16 hours. The solvent was evaporated under reduced pressure, leaving a residue which was passed through a column of silica gel, eluting with methylene chloride. The product-containing fractions were combined, washed with an aqueous solution of sodium hydroxide, dried over anhydrous magnesium sulfate, and the solvent evaporated under reduced pressure, yielding 16.85 g of 4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 16 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customleaving a residue which
  5. washeluting with methylene chloride
  6. washwashed with an aqueous solution of sodium hydroxide
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-e8fbb7ce8b3b4553b3ab175de9ec28ca
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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