Propanal → 4-Nitro-3-hexanol

HRID 909991Notes

Reaction equation

HRID 909991 reaction equation
[N+:1](CCC)([O-:3])=[O:2].[CH2:7]1[CH2:17][CH2:16]N2[C:10](=NCCC2)[CH2:9][CH2:8]1.C(=[O:21])CC>C(OCC)(=O)C>[OH:21][CH:7]([CH2:17][CH3:16])[CH:8]([N+:1]([O-:3])=[O:2])[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 527PropanalHCID 79031-NitropropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 2206384-Nitro-3-hexanolYield 837.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A reaction vessel was replaced with nitrogen, and 1-nitropropane (8.93 ml, 100 mmol) and dry-THF (50 ml) were added. After DBU (1,8-diazabicyclo[5.4.0]-7-undecene) (1.5 ml, 10 mmol) had been added, propionaldehyde (4.68 ml, 100 mmol) was added while the vessel was cooled in an ice bath. After the mixture had been stirred at room temperature for 10 hours, ethyl acetate (100 ml) was added, and the whole was washed with dilute hydrochloric acid, water, and a saturated salt solution. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to yield 4-hydroxy-3-nitrohexane (12.33 g, 84% yield).

Workup

  1. dry with materialdry-THF (50 ml)
  2. additionwere added
  3. temperaturewas cooled in an ice bath
  4. washthe whole was washed with dilute hydrochloric acid, water
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d86b3209a13340678209556d5317e7fd
Source dataset
uspto-grants-2011_09
Patent number
US08021915B2

Reaction notes

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