Methanol → 2-(4-Nitrophenyl)butanol

HRID 1074442Notes

Reaction equation

HRID 1074442 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:14][CH3:15])[C:11](O)=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].CO>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH2:14][CH3:15])[CH2:11][OH:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 240472-(4-Nitrophenyl)butyric acid

Product 1

HCID 204966922-(4-Nitrophenyl)butanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 20.9 g of 2-(4-nitrophenyl)butyric acid in 500 ml of dry tetrahydrofuran was added, dropwise, 1.1 equivalents of 10 M borane-dimethylsulfide complex in 100 ml of dry tetrahydrofuran. The mixture was stirred at room temperature for 1.5 hours and then refluxed for 1.5 hours and finally cooled to room temperature. Methanol (10 ml) was added, the mixture was stirred for 30 minutes, and the solvent was then evaporated under reduced pressure. The residue was dissolved in 100 ml of methanol and the solvent was evaporated and this procedure was repeated three (3) times. The resulting oil was purified by chromatography on silica gel, eluting with 1:1 ethyl acetate/hexane to give 2-(4-nitrophenyl)butanol as a light-yellow oil.

Workup

  1. temperaturerefluxed for 1.5 hours
  2. temperaturefinally cooled to room temperature
  3. stirringthe mixture was stirred for 30 minutes
  4. customthe solvent was then evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in 100 ml of methanol
  6. customthe solvent was evaporated
  7. customThe resulting oil was purified by chromatography on silica gel
  8. washeluting with 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-b7075177e6024583b3104666f58b59d3
Source dataset
uspto-grants-1983_07
Patent number
US04391818

Reaction notes

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