From: Jason Smith (loggin1270$##$hotmail.com)
Date: Sun Sep 02 2007 - 05:59:44 EDT
I could not find the attachment you mentioned however i will place below a
procedure that I have used for a similar compound with great success several
years ago. On the topic of the brown oil, it is quite possible that you
product is contained within this oil and that recrystalisation or a column
with yield your product. Have you tried to see if any of the the spots match
by TLC to the product (if you have access to a sample of the product)? Below
i have attached a procedure for nitration of a similar compound. I would
venture however that you can isolate your product from the oil. Do keep me
informed of your progress.
Preparation of p-Nitroacetanilide
Add 5 g of finely powdered, dry acetanilide to 5 mL of glacial acetic acid
contained in a 100
mL beaker: introduce slowly into the well stirred mixture 10 mL of
concentrated sulfuric acid.
The mixture becomes warm and a clear solution results. Surround the beaker
with a mixture of ice
and water. Prepare a mixture of 3 mL of concentrated nitric acid and 2 mL of
concentrated
sulphuric acid in a 20 mL (150 mm x 50 mm) test tube. Clamp the test tube
using a retort stand.
When the temperature of the solution in the beaker falls to 4 – 5 °C, add in
the mixture of acids
from the test tube (using a Pasteur pipette) very slowly. During the
addition of the mixed acids, the
contents of the beaker should be stirred with a stirring rod, and the
temperature should be
maintained below 10°C. After the mixed acid has been added, remove the
beaker from the freezing
mixture, and allow it to stand at room temperature for 30 minutes. Pour the
reaction mixture on to
about 150 mL of crushed ice in a 250 mL beaker, whereby the crude
nitroacetanilide is at once
precipitated. Allow to stand for 15 minutes, filter with suction on a
Buchner funnel, wash it
thoroughly with cold water until free from acids (test the wash water) and
drain well. Save about
0.1 g of this crude material for TLC. Then recrystallise the remainder of
the pale yellow product
from the minimum quantity of hot ethanol, filter at the pump using clean
apparatus and dry in air
upon filter paper. (Make sure that the Buchner flask used in the filtration
is clean, because the
filtrate which contains the o-nitroacetanilide must be saved for examination
by TLC). The pnitroacetanilide
is a colourless solid of m.p.214 °C.
Investigate by thin-layer chromatography (TLC), using the silica gel plates
provided, the
effectiveness of the recrystallisation process. On your plates you should
have spots of acetone
solutions of the crude and the recrystallised products. In addition, a spot
of a concentrated
portion of the ethanolic mother-liquor (from the recrystallistion) should be
applied to the plate.
Develop the chromatogram with a toluene - ethyl acetate mixture (4:1 v/v.)
and dry the plate in an
oven at 100 °C. Using a pencil, mark the position of any visible spots.
Examine the plate in
ultraviolet light and again mark the visible spots with a pencil. Finally
place the plate in a tank of
Department of Chemistry and Biomolecular Sciences, Macquarie University
CHEM204, 2005
iodine vapour to see if anything else becomes visible. The recrystallised
p-nitroacetanilide (Rf
0.07) should be free from the pale yellow o-isomer (Rf 0.36); these
components are revealed in
ultraviolet light or by iodine. In addition to both o- and
p-nitroacetanilide, the mother-liquor
should contain p-nitroaniline (Rf 0.24) and o-nitroaniline (Rf 0.45). If the
solution of the motherliquor
which is applied to the silica plate is sufficiently concentrated, the
nitroaniline spots will
become visible before examination in ultraviolet light or iodine treatment.
If this is not the case,
the nitroaniline spots should become visible in ultraviolet light or by
iodine treatment. Further
characterise your product by taking an IR.
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