Acetone → HCID 22157927, compound

A solution of 1 mol of 3-(3-methylbenzyl)-butanone (86% pure) in 300 ml of isopropanol was added drop-wise in the course of 5 hours to 100 g of aluminum triisopropylate heated to boiling with 300 ml of isopropanol, while a mixture of acetone and isopropanol distilled off slowly through a 50-cm long packed column. After reacting for 8 hours, the distillate no longer contained any acetone. The residual isopropanol was then distilled off and 300 ml of toluene, 300 g of ice and 300 g of conc. hydrochloric acid were added to the residue. The layers were separated, the aqueous phase was extracted with 300 ml of toluene, and the combined organic phases were extracted by shaking with a little water, concentrated and distilled through a Vigreux column at 0.2 mbar. A mixture of 1-(3-methylphenyl)-2-methylbutan3-ol isomers was obtained in 85% yield from 78°-80° C.

1. temperatureheated
2. distillationdistilled off slowly through a 50-cm long packed column
3. distillationThe residual isopropanol was then distilled off
4. addition300 ml of toluene, 300 g of ice and 300 g of conc. hydrochloric acid were added to the residue
5. customThe layers were separated
6. extractionthe aqueous phase was extracted with 300 ml of toluene
7. extractionthe combined organic phases were extracted
8. concentrationconcentrated
9. distillationdistilled through a Vigreux column at 0.2 mbar
10. additionA mixture of 1-(3-methylphenyl)-2-methylbutan3-ol isomers
11. customwas obtained in 85% yield from 78°-80° C.

ORD record

ord-acb9b545c63740efb74fb1ce9b88e0c7

Source dataset

uspto-grants-1990_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04968668