Water → 1-(Nitromethyl)cyclopentanol

HRID 44692Notes

Reaction equation

HRID 44692 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[O-]CC.[Na+].O.[N+:12]([CH3:15])([O-:14])=[O:13]>C(O)C>[N+:12]([CH2:15][C:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 8452CyclopentanoneHCID 2723922Sodium ethoxide

Product 1

HCID 112865391-(Nitromethyl)cyclopentanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of cyclopentanone (40.0 mL, 452 mmol) in nitromethane (36 mL) and ethanol (14 mL) was added a solution of sodium ethoxide in ethanol (2.67 M, 8.5 mL, 23 mmol). The solution was stirred for 5 d at rt. Water (400 mL) was added and the mixture was extracted with ethyl acetate (2×350 mL). The combined organic extracts were washed with water (2×200) and brine (200 mL), dried over MgSO4, filtered, and concentrated. The starting materials and solvent were removed from the product by distillation under reduced pressure to yield 1-(nitromethyl)cyclopentanol as a yellow liquid, 8.3 g (13%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×350 mL)
  2. washThe combined organic extracts were washed with water (2×200) and brine (200 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe starting materials and solvent were removed from the product by distillation under reduced pressure

Sources & evidence

ORD record
ord-758b210176f9456aac3d3403051256cc
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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