Water → 1-(Nitromethyl)cyclobutanol

HRID 44705Notes

Reaction equation

HRID 44705 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)cyclobutanolYield 45%

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 d at rt. Water was added and the mixture was extracted thrice with ethyl acetate. 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 1-(nitromethyl)cyclobutanol as a yellow liquid (8.51 g, 45%).

Workup

  1. extractionthe mixture was extracted thrice with ethyl acetate
  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-8bb917cdce074265b410e9de4d4fef51
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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