Nitric Acid → 2-Hydroxymethyl-2,4,6,7-tetramethyl-5-nitrodihydrobenzofuran

HRID 1987774Notes

Reaction equation

HRID 1987774 reaction equation
[OH:1][CH2:2][C:3]1([CH3:15])[CH2:7][CH:6]2[CH:8]([CH3:14])[CH:9]=[C:10]([CH3:13])[C:11]([CH3:12])=[C:5]2[O:4]1.[N+:16]([O-])([OH:18])=[O:17]>C(O)(=O)C>[OH:1][CH2:2][C:3]1([CH3:15])[CH2:7][CH:6]2[CH:8]([CH3:14])[C:9]([N+:16]([O-:18])=[O:17])=[C:10]([CH3:13])[C:11]([CH3:12])=[C:5]2[O:4]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 688473332-Hydroxymethyl-2,4,6,7-tetramethyldihydrobenzofuran

Product 1

HCID 688476092-Hydroxymethyl-2,4,6,7-tetramethyl-5-nitrodihydrobenzofuran

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

2.3 g of 2-hydroxymethyl-2,4,6,7-tetramethyldihydrobenzofuran was dissolved in 30 ml of anhydrous acetic acid and 1.9 ml of nitric acid was added dropwise while stirring at 0° C. After stirring at 0° C. for one hour, the solution was poured into ice-water, followed by stirring at room temperature for one hour. The reaction solution was extracted with ether, washed with saturated saline and dried over anhydrous magnesium sulfate and, after the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography (chloroform) to obtain 1.34 g of the objective product.

Workup

  1. stirringAfter stirring at 0° C. for one hour
  2. stirringby stirring at room temperature for one hour
  3. extractionThe reaction solution was extracted with ether
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationafter the solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-5498497bdf2647b990379931e6dea0ec
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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