1-Butanol → 1-(Dibutoxymethyl)-2-nitrobenzene

HRID 552074Notes

Reaction equation

HRID 552074 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O-:3])=[O:2].[CH2:12]([OH:16])[CH2:13][CH2:14][CH3:15].O.[C:18]1(C)[CH:23]=CC(S(O)(=O)=O)=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH2:23]([O:7][CH:6]([O:16][CH2:12][CH2:13][CH2:14][CH3:15])[C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 111012-NitrobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 150331791-(Dibutoxymethyl)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution comprising 2-nitrobenzaldehyde (4.53 g, 30.0 mmol), 1-butanol (13.7 ml, 150 mmol) and toluene (60 ml) was added with p-toluene sulfonic acid monohydrate (57 mg, 0.300 mmol) and molecular sieves-4A (1 g), and refluxed for two days. The mixture was filtered through celite, washed with saturated sodium bicarbonate and saturated sodium chloride water, and then dried with anhydrous magnesium sulfate. The solution was concentrated to obtain Step 1 compound (8.43 g, quant) as a brown oily substance.

Workup

  1. temperaturerefluxed for two days
  2. filtrationThe mixture was filtered through celite
  3. washwashed with saturated sodium bicarbonate and saturated sodium chloride water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationThe solution was concentrated
  6. customto obtain Step 1 compound (8.43 g, quant) as a brown oily substance

Sources & evidence

ORD record
ord-b870e373095c4260958f2cae81581c84
Source dataset
uspto-grants-2011_05
Patent number
US07951799B2

Reaction notes

Loading…