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Acetylation of boric acid; Triacetyl Borate

SyntheticPage 806
DOI: 10.1039/SP806
Submitted Jan 13, 2016, published Jun 10, 2016
Jevica Salim (jev340@gmail.com), Steven Kennedy (Steven.Kennedy@millersville.edu)
A contribution from Kennedy Group, Millersville University


			Reaction Scheme: <IMG src="/images/empty.gif">Acetylation of <SPAN id=csm1465561560813 class=csm-chemical-name title="boric acid" grpid="1">boric acid</SPAN><IMG src="/images/empty.gif">

Chemicals Used

Boric acid (Sigma Aldrich)
Acetic Anhydride (Alfa Aesar)
Acetic Acid (Fisher Scientific)
Toluene (Sigma Aldrich)

Procedure

B(OH)3 (25 g, 0.4 mol), acetic acid (1.25 mL), and toluene (115 mL) were added to a three-necked round bottom flask equipped with a condenser and a thermometer. The mixture was stirred for thirty minutes at room temperature before addition of acetic anhydride (116 mL, 1.2 mol). The reaction temperature was raised to 45 ºC over one hour and then to 60 ºC over one and a half hours. The mixture was left to stir overnight. When the reaction completed, the cloudy-white mixture turned clear and the solution was cooled to room temperature. The precipitated B(OAc)3 was isolated by filtration under dry N2 as white powder (36.95 g, 48 % yield).

Author's Comments

Use freshly opened bottle of acetic anhydride if possible.



Data

1H NMR (400 MHz, DMSO-d6) δ ppm 1.884 (s, 9H).

13C NMR (100 MHz, DMSO-d6) δ ppm 21.47, 172.50.

Lead Reference

Ritscher, J. S.; Kowalski, D. C.; McKeon, J. E. J. Chem. Ed. 1974, 51 (10), 688.

Supplementary Information

1H_NMR_B(OAc)3.PNG
13C_NMR_B(OAc)3.PNG
Reaction_Setup.jpg
Filtration.jpg

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Get structure file (.cdx, .sk2, .mol)

Keywords: Boron triacetate, Lewis acid

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