Acetic Acid → 1-Cyclopropyl-2-nitroethan-1-ol

HRID 1714866Notes

Reaction equation

HRID 1714866 reaction equation
[CH:1]1([CH:4]=[O:5])[CH2:3][CH2:2]1.[N+:6]([CH3:9])([O-:8])=[O:7].[OH-].[Na+].CC(O)=O>CO.O>[CH:1]1([CH:4]([OH:5])[CH2:9][N+:6]([O-:8])=[O:7])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 123114Cyclopropanecarboxaldehyde

Product 1

HCID 193693201-Cyclopropyl-2-nitroethan-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of cyclopropanecarbaldehyde (1.4 g, 20 mmol) and nitromethane (1.2 g, 20 mmol) in MeOH at 0° C. was added a solution of NaOH (840 mmol, 21 mmol) in water (8 mL). The mixture was stirred at room temperature for 1 h and then HOAc (1.3 mL) was added. Volatile solvent was removed in vacuo. The residue was diluted with water and extracted twice with EtOAc. The combined EtOAc extracted was washed with brine, dried (Na2SO4) and concentrated to give the title compound as a yellow liquid.

Workup

  1. customVolatile solvent was removed in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted twice with EtOAc
  4. extractionThe combined EtOAc extracted
  5. washwas washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0ddb326dddb7437489cf99150879dbce
Source dataset
uspto-grants-2010_09
Patent number
US07799787B2

Reaction notes

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