Synthesis of aluminum tert-butoxide

Preparation of aluminum tert-butoxide

Preparation of aluminum tert-butoxide (aluminum tert-butylate; aluminum tert-butanolate)

Preparation of aluminum tert-butoxide (aluminum tert-butylate; aluminum tert-butanolate)

A dry flask with a ground glass joint carrying a reflux condenser protected with a calcium chloride tube is charged with 40 grams of amalgamated aluminum alloy turnings and 200 ml of t-butyl alcohol (distilled over sodium) and heated in an oil bath. If the reaction does not begin after refluxing for 1 hour, as shown by darkening of the solution, about 5 g. of aluminum t-butoxide or other starter is added (the addition of a small amount of one of the following reagents may prove helpful: mercuric chloride with shaking, aluminum isopropoxide, aluminum activated with iodine; the reagent obtained after any of these treatments is not suitable for use in an oxidation but serves as a catalyst for preparing reagent which is adequate for such use). Once in progress, the reaction proceeds to completion after gentle refluxing for 10-15 hours, during which time 500-600 ml of benzene are added to keep the alkoxide in solution. When hydrogen evolution has stopped, the warm mixture is centrifuged and the sediment is stirred with hot benzene and centrifuged; the addition of a little moist ether may be of assistance in obtaining a clear solution. The clear extracts are combined and evaporated, at first at ordinary pressure and then vacuum. The colorless aluminum 2-butoxide weighs 155-165 grams and should be kept in a well-stoppered bottle.

Rec. trav. chim., 56, 137, 1937
J. Am. Chem. Soc., 60, 1158, 1938
Experiments in Organic Chemistry, L. F. Fieser, 445, 1941

IUPAC Name

aluminum;2-methylpropan-2-olate

InChI

InChI=1S/3C4H9O.Al/c3*1-4(2,3)5;/h3*1-3H3;/q3*-1;+3

InChI Key

MDDPTCUZZASZIQ-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-].[Al+3]

Depositor-Supplied Synonyms

Aluminum tert-butoxide, Aluminum tert-butylate, Aluminum tert-butanolate, Aluminum tri-tert-butoxide, Tri-tert-butoxyaluminum, Aluminum, tri-tert-butoxy-, Aluminum, tris-tert-butoxy-, 144501-46-2, aluminium t-butoxide, aluminum tri-t-butoxide, tri-tert-butoxy aluminum, AC1L29NS, UNII-6D623JMP3R, Aluminium tri-tert-butanolate, 6D623JMP3R, aluminum 2-methylpropan-2-olate, MDDPTCUZZASZIQ-UHFFFAOYSA-N, NSC 4648, EINECS 209-146-1, AR-1H6911, AKOS015841134, aluminum tris(2-methylpropan-2-olate), RTR-031051, tert-Butyl alcohol, aluminum salt (8CI), TR-031051, A0804, aluminium(3+) ion tris(2-methylpropan-2-olate), I14-51716, 3B3-034186, 200575-20-8, 3099-76-1, 344914-50-7, 856321-03-4

Removed Synonyms

CID68399, 2-Propanol, 2-methyl-, aluminum salt, 2-Propanol, 2-methyl-, aluminum salt (3:1), 556-91-2, 572-41-8

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