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This file is a part of the Rhodium site archive. This Aug 2004
static snapshot is hosted by Erowidas of May 2005 and is not being
updated. > > Back to Rhodium Archive Index > >
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S Y N T H E S I S O F M D P 2 P F R O M 1 , 3 - B E N Z O D I O
X O L E
B Y F R I E D E L - C R A F T S A L K Y L A T I O N W I T H 2 -
N I T R O P R O P E N E
W R I T T E N B Y SC O O B Y DO O
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To a 3-necked 500 ml flask under a nitrogen atmosphere was added
300 mL of dry DCM, 0.1 mole of 2-
Nitropropene(8.7g) and 0.5 moles of 1,3-Benzodioxole (61 g). The
flask was then secured within a dewar flask
sitting on top of a magnetic stirplate. Dry ice was added to the
dewar flask which was filled with acetone until a
temperature of approx -78C was acquired. Once the internal flask
temperature of -70C was reached, 0.1mole (19 g) of TiCl4was dripped
slowly into the stirred solution. The temp started to rise so the
addition was
controlled to keep the internal flask temp around -60C to -70C.
The flask was then stirred for 30 mins at -70C, by which time the
precipitate which formed from the addition had dissipated. The
dewar flask wasremoved and the stirring solution was allowed to
warm up to room temperature, during which time the black
solution w ill change viscosity and colour.
To hydrolyze the formed nitro-titanium complex, 100 mls of water
was added to the solution which was then
refluxed for 2 hours. During the reflux a brown gas (probably
NO2) is evolved. The flask was cooled and vacuum
filtered (cleans it up a lot) the water layer seperated and
discarded. The organic layer was then washed with
3x200 mL of 10% NaOH and 1x200 mL of a brine solution. It was
then dried with magnesiumsulfate, the DCM
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evaporated and resulting orange-yellow oil vacuum distilled. The
1,3-Benzodioxole came over at 40-45 C at 10
mbar then a yellow-green fluorescent oil (MDP2P) began
distilling at 135C at 3 mbar.
8 grams of MDP2P was collected,
corresponding to 45% yield from 2-
Nitropropene or 23.5% from 1,3-
Benzodioxole (calculated on the
amount of 1,3-Benzodioxole not
recovered during workup).
Reference:Tetrahedron Letters, Vol 29, No 24, pp. 2977-2978
(1988)
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