Nitromethane → 1-Nitrononadecan-2-ol

HRID 583960Notes

Reaction equation

HRID 583960 reaction equation
[CH:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[N+:20]([CH3:23])([O-:22])=[O:21]>CCOCC>[N+:20]([CH2:23][CH:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 6375NitromethaneHCID 12533Octadecanal

Product 1

HCID 155003461-Nitrononadecan-2-olYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of octadecanal (9a) (2.22 g, 8.28 mmol) and nitromethane (1.52 g, 24.90 mmol) in anhyd Et2O (10 mL), Amberlyst A-21 (1.2 g) was added at r.t. The mixture was stirred and heated at reflux for 48 h. After removal of the Amberlyst A-21 by filtration, the filtrate was concentrated under reduced pressure. Flash column chromatography of the residue (EtOAc/petroleum spirit, 5/95) gave 1-nitrononadecan-2-ol (10a) (2.41 g, 89%) as a white solid; mp 55-56° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 h
  3. customAfter removal of the Amberlyst A-21
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1a66b4f4fd6443ebb7a9425d7f95a691
Source dataset
uspto-grants-2005_08
Patent number
US06924309B2

Reaction notes

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