Benzaldehyde → 2-Nitro-1-phenylbutan-1-ol

HRID 2107366Notes

Reaction equation

HRID 2107366 reaction equation
[Li]CCCC.[N+:6]([CH2:9][CH2:10][CH3:11])([O-:8])=[O:7].[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>C1COCC1.C(Cl)Cl>[C:13]1([CH:12]([OH:19])[CH:9]([N+:6]([O-:8])=[O:7])[CH2:10][CH3:11])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 6049Ethylenediaminetetraacetic AcidHCID 79031-NitropropaneHCID 178418339Butyllithium

Product 1

HCID 2261232-Nitro-1-phenylbutan-1-olYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (1.6 M in hexane, 6.24 mL) was added dropwise with stirring to a solution of nitropropane (0.9 mL, 10 mmol) in THF (12 mL) at -78° C. After 15 minutes a solution of TiCl3 (OPriso) (5 mmol) in THF (2 mL) and CH2Cl2 (3 mL) solution was added. After a further 15 minutes benzaldehyde (0.5 mL, 5 mmol) was added and the mixture allowed to warm up to room temperature (~ 30 min.). Stirring was continued for a further 3.5 hours at room temperature and the mixture was quenched with an aqueous slurry of disodium EDTA (1.86 g, 5 mmol) and extracted with Et2O (3×75 mL). The combined Et2O fractions were washed with dilute hydrochloric acid (2 M, 75 mL), aqueous sodium bicarbonate (75 mL) and water (75 mL), dried and evaporated in vacuo. Flash column chromatography (SiO2 , hexane:Et2O, 6:1 v.v] gave 1-phenyl-2-nitro-butan-1-ol (0.57 g, 61%) erythro:threo ratio 6:1.

Workup

  1. extractionextracted with Et2O (3×75 mL)
  2. washThe combined Et2O fractions were washed with dilute hydrochloric acid (2 M, 75 mL), aqueous sodium bicarbonate (75 mL) and water (75 mL)
  3. customdried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-d5df211f5cf54063b248e2b7120c0891
Source dataset
uspto-grants-1990_06
Patent number
US04933505

Reaction notes

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