Acetic Acid → HCID 10012389, compound

HRID 455681Notes

Reaction equation

HRID 455681 reaction equation
[OH-].[Na+].[N+:3]([CH3:6])([O-:5])=[O:4].[CH:7]1([CH:13]=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(O)(=O)C>CCO>[CH:7]1([CH:13]([OH:14])[CH2:6][N+:3]([O-:5])=[O:4])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 16275Cyclohexanecarboxaldehyde

Product 1

HCID 10012389HCID 10012389, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 M aqueous NaOH (8.31 mL, 83 mmol) was added dropwise via addition funnel to a solution of nitromethane (4.46 mL, 83 mmol) and cyclohexanecarboxaldehyde (10 mL, 83 mmol) in EtOH (20 mL) at 0° C. with vigorous stirring. The resulting white slurry was stirred 10 minutes and became a white solid. Acetic acid (4.76 mL, 83 mmol) was added and the reaction was partitioned between diethyl ether and water. The layers were separated and the aqueous layer was extracted with diethyl ether. The combined organic extracts were washed with water, saturated aqueous sodium chloride, and dried over magnesium sulfate. The solution was filtered and concentrated in vacuo and dried under vacuum to afford 1-cyclohexyl-2-nitroethanol. The product was used directly for the next step without further purification.

Workup

  1. customthe reaction was partitioned between diethyl ether and water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with diethyl ether
  4. washThe combined organic extracts were washed with water, saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customdried under vacuum

Sources & evidence

ORD record
ord-df0f77627fbe4c14a54ce02cef287b20
Source dataset
uspto-grants-2013_07
Patent number
US08497264B2

Reaction notes

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