4-Hydroxybenzyl Alcohol → 4-(2-Methyl-2-nitropropyl)phenol

HRID 2172706Notes

Reaction equation

HRID 2172706 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[N+:10]([CH:13]([CH3:15])[CH3:14])([O-:12])=[O:11].CC(C)([O-])C.[K+]>COCCOCCOC>[CH3:14][C:13]([N+:10]([O-:12])=[O:11])([CH3:15])[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 3982-NitropropaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 128269024-(2-Methyl-2-nitropropyl)phenolYield 83%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A mixture of 4-(hydroxymethyl)phenol (1.0 g, 8.1 mmol) and 2-nitropropane (4.0 g, 45 mmol) in diglyme (50 mL) was cooled in an ice bath. Potassium tert -butoxide (0.45 g, 4.0 mmol) was added in portions, then the reaction mixture was heated to reflux overnight. After cooling, the mixture was concentrated and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give 4-(2-methyl-2-nitropropyl)phenol (1.3 g, 83% yield) as a light yellow solid.

Workup

  1. temperaturewas cooled in an ice bath
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux overnight
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated
  6. customthe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-35dfa0b1e50f4de7b8d86841e6d65f5f
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

Loading…