Water → 1-(Nitromethyl)cyclopentanol

HRID 1469230Notes

Reaction equation

HRID 1469230 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-f365faa68ca94449841d6ce014a2b3d2
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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