Natural Science Forum / Chemistry / Organic Synthesis / December 2003

Hey all, I have not posted in here for a wile but I have been wondering, I
finally found a interesting route to the nitrostyrene. The procedure looks
accurate enough, But sadly that ratios they are using are to small, In
theory the ratio or mmol can up scaled up right? I was thinking about it and
it would be possible but that factors will change,? Heat length et cetera et
cetera, Can any one give me some insight on the possibilities of scaling the
procedure up, Of course this would all be theoretical I just want to find
out if its at all possible to scale up with ease,

2,5-dimethoxybenzaldehyde (1.97 g, 11.8 mmol) and nitromethane
(0.72 g, 11.8 mmol) in methanol (200 mL) was stirred at room temperature
until
the solids dissolved. The solution was cooled to 0 deg C and a 10.5 M NaOH
solution (2 mL) was added dropwise over 20 min. The alkaline solution was
added
slowly to a 4% HCl solution (200 mL) maintained at 60 deg C. The pale yellow
amorphous solid that formed was filtered and washed with water (200 mL). The
crude product was recrystallized from absolute ethanol to give yellow
needles
(2.11 g, 85%)

Preparation of 10.5 M NaOH: Dissolve 10.5g sodium hydroxide under cooling
in 20ml water, and after cooling dilute the solution to exactly 25ml.

REF (JOC 1987, 52, 2945-2947)

Thanx