Water → 1-(Nitromethyl)cyclobutanol

HRID 547313Notes

Reaction equation

HRID 547313 reaction equation
[C:1]1(=[O:5])[CH2:4][CH2:3][CH2:2]1.[N+:6]([CH3:9])([O-:8])=[O:7].[O-]CC.[Na+].O>C(O)C>[N+:6]([CH2:9][C:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1)([O-:8])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 14496CyclobutanoneHCID 2723922Sodium ethoxide

Product 1

HCID 132308351-(Nitromethyl)cyclobutanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of cyclobutanone (10.0 g, 143 mmol) and nitromethane (12 mL) in ethanol (10 mL) was added sodium ethoxide in ethanol (2.67 M, 2.7 mL, 7.2 mmol). The mixture was stirred for 6 days at room temperature. Water was added and the mixture was extracted with ethyl acetate (3×). The organic phases were combined, washed with water and brine, dried over Na2SO4, filtered, and concentrated. The volatiles were removed by distillation under vacuum to provide 8.51 g of 1-(nitromethyl)cyclobutanol as a yellow liquid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe volatiles were removed by distillation under vacuum

Sources & evidence

ORD record
ord-0845f259051d4d98ba5da202a4c2378a
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

Loading…