Structure of 13352-78-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 13352-78-8 |
Formula : | C10H22O9 |
M.W : | 286.28 |
SMILES Code : | COCOCOCOCOCOCOCOCOC |
MDL No. : | MFCD26792353 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; at 55 - 115℃;Inert atmosphere; | Paraformaldehyde (45 g 1.5 mol, 30 g/mol CH2O eq.) was weighed into a 500 ml. heavy walled glass reactor fitted with an O-ring joint with a polytetrafluoroethylene (PTFE) seal and KONTES 0-4 mm Hivac Stopcock (Kontes Glass Company, Vineland, New Jersey, United States of America). A magnetic stirrer bar was introduced and the joint sealed. The reactor was flushed with dry nitrogen. Methylal (48 mL, 41.3 g, 0.54 mol) was added and stirring at 100 rpm was initiated. After thorough mixing, 1.0 mL (2 g) reagent grade sulfuric acid was added. The hotplate-stirrer was set to 55 0C and after a minute or so of boiling when methylal vapor reached the stopcock base, the stopcock was closed. At 30 minute intervals the temperature was raised to 65 0C, 75 0C, then to 85 0C where it remained overnight. The next day the temperature was increased at 2 hour (hr) intervals to 95 0C, 105 0C and to 1 15 0C overnight. The next day the reactor was cooled while stirring, opened and the contents were neutralized and made basic by careful addition of 100 ml. of sodium methoxide/methanol solution made by reacting/dissolving 1.6 g freshly cut sodium metal in 100 mL of dry methanol.The mixture of solid and liquid was filtered using a Buchner funnel and cellulose filter paper. The solid was washed several times with dry methanol. The washings were added to the filtrate. The combined filtrate washings were transferred to a 250 mL 14/20 flask with stir-bar and rigged for fractional distillation through a 12 cm Vigreaux column. Methanol/methylal was distilled off until the head reached 70 0C. The pot material, a mixture of liquid and solid, was transferred to a 100 mL 14/20 flask and rigged for high vacuum distillation in a special still designed to strip volatiles from lower volatility oil under dynamic vacuum. Thus residual methanol, methylal, trioxane and CH3O(CH2O)nCH3 (n = 2 and 3) were removed while the distilling oil (5-10 mL) was identified by 1H NMR as almost pure CH3O(CH2O)4CH3, a free-flowing colorless oil. The approximately 20 mL of pot residue semi-solidified on cooling and was extracted with chloroform to yield about 10 mL Of CH3O(CH2O)nCH3 (n = 6 and 7), an oily colorless liquid, confirmed by 1H NMR after removal of the chloroform.The filter cake from the Buchner filtration was placed in a cellulose extraction thimble and extracted with chloroform in a Soxhlet extractor for two days. On removal of the chloroform the extract yielded about 15 grams of CH3O(CH2O)nCH3 (n = 8-13) which yielded about 5 grams of the oligomer where n= 8 and 9, a waxy semisolid, which was petroleum ether soluble, and about 5 g of n = 1 1-13, a white friable solid, which was insoluble in petroleum ether. |