I have reacted my compound with tetrabutylammoniumhydroxide. now I want to remove excess of tetrabutylammoniumhydroxide but both my compound and tetrabutylammoniumhydroxide soluble in organic part.
how can I remove tetrabutylammoniumhydroxide form solution
Is your compound stable to alumina or silica? You could run it through a quick plug, which should grab the TBAOH because it is ionic. Recrystallizing from MeOH, EtOH, oriPrOH would work too if your compound can be crystallized from those solvents. TBAOH would be somewhat soluble in those solvents. Good luck!
Hi Avinash Dhamija
Removal of Tetramethylammonium Hydroxide From Solution Using Ion Exchange. Ion exchange is used to remove tetramethylammonium hydroxide from an aqueous solution. Both strong acid cation (SAC) and weak acid cation (WAC) exchange resins show excellent uptake of the TMA+ ion. The pseudo-second-order kinetic model fits the data of uptake rate well. When using an SAC exchange resin, the pH does not affect the uptake efficiency, while that of the WAC exchange resin is strongly affected by the pH. Regeneration experiments show excellent performance of resins after five cycles. The selectivity coefficient of TMA+ over H+ for SAC is calculated as 5.16, while for WAC, in the bulk solution, the selectivity coefficient is notably lower (6.45×10-4). The presence of competing ions interfere with the TMA+ uptake, of which Mg2+ has the most notable effect. The ion exchange model is applied to obtain resin selectivity over the TMA+ ion as well. See: H. M. Citraningrum ; Department of Chemical Engineering, National Taiwan University of Science and Technology, Taipei, Taiwan ; J. C. Liu ; J. M. Chern
Please, find in attach a related paper to your question by:Jie Li and Pengcheng Huang, published in Beilstein J. Org. Chem. 2011, 7, 426–431, it may be useful for you.
General procedure for the deprotection reaction using Bu 4 NOH as base with CH 3 OH in toluene: Under a nitrogen atmosphere, 4-aryl-2-methyl-3-butyn-2-ol (2 mmol) was dissolved into anhydrous toluene (100 mL) and the solution was heated to 75 °C, then Bu4NOH, 40 wt % solution in CH3OH (Bu4NOH: 0.1 mol per 1 mol 2-hydroxypropyl group) was added. The mixture was stirred at 75 °C for the indicated time. After cooling down to room temperature, the mixture was washed successively with 5% HCl and brine, dried over MgSO4, and concentrated in vacuo. The crude product was then purified by column chromatography to afford the product.
thank you Mr. kyle and Mr. talaat for your suggestions. I will definitely try these.
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