Propanal → 4-Nitro-3-hexanol

HRID 732323Notes

Reaction equation

HRID 732323 reaction equation
[N+:1](CCC)([O-:3])=[O:2].[O:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.N12CCCN=C1CCC[CH2:14][CH2:13]2.C(=O)CC>C(OCC)(=O)C>[OH:7][CH:8]([CH2:13][CH3:14])[CH:9]([N+:1]([O-:3])=[O:2])[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 527PropanalHCID 79031-NitropropaneHCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 2206384-Nitro-3-hexanolYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a reaction vessel purged with nitrogen, 1-nitropropane (8.93 ml, 100 mmol) and dehydrated tetrahydrofuran (dry THF) (50 ml) were added. After 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (1.5 ml, 10 mmol) was added, propionaldehyde (4.68 ml, 100 mmol) was added while cooling in an ice bath. After stirring for 10 hours at room temperature, ethyl acetate (100 ml) was added. The resulting solution was washed using dilute hydrochloric acid, water and saturated saline, and the obtained organic layer was dried over anhydrous sodium sulfate. The resulting solution was concentrated under reduced pressure to give 4-hydroxy-3-nitrohexane (12.33 g, yield 84%)

Workup

  1. additionwere added
  2. temperaturewhile cooling in an ice bath
  3. washThe resulting solution was washed
  4. dry with materialthe obtained organic layer was dried over anhydrous sodium sulfate
  5. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7a86a1c25ad648bfa7d1c7a5b08fe20c
Source dataset
uspto-grants-2009_09
Patent number
US07586117B2

Reaction notes

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