Iodine → 2,2-Dimethyl-5-hexyn-3-ol

Temperature

-60 °C

26 g (0.96 mol) of aluminum flakes were covered with a layer of 120 ml of tetrahydrofuran, and a few grains of iodine and a pinch of mercury (II) chloride were added. After 12 hours, a solution of 169 g (1.42 mol) of propargyl bromide in 170 ml of tetrahydrofuran was added dropwise at 60° C., while stirring vigorously. The mixture was then cooled to -60° C., and in the course of 2 hours, a solution of 293.8 g (1 mol) of 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-one in 330 ml of tetrahydrofuran was stirred in. 340 ml of a saturated ammonium chloride solution were then added to the reaction mixture at 0° C. The bulk of the solvent was distilled off under reduced pressure, and the residue was extracted with twice 600 ml of ethyl acetate. After the organic phase had been washed with water, it was dried over anhydrous sodium sulphate and then concentrated under reduced pressure. The precipitated crystalline product was filtered off and washed with isopropanol and diethyl ether. 131.1 g (39.3% of theory) of 4-(4-chlorophenoxy)-(1-H-1,2,4-triazol-1-yl)-methyl)-5,5-dimethyl-1-hexyn-4-ol of melting point 124° to 125° C. were obtained.

1. distillationThe bulk of the solvent was distilled off under reduced pressure
2. extractionthe residue was extracted with twice 600 ml of ethyl acetate
3. washAfter the organic phase had been washed with water, it
4. dry with materialwas dried over anhydrous sodium sulphate
5. concentrationconcentrated under reduced pressure
6. filtrationThe precipitated crystalline product was filtered off
7. washwashed with isopropanol and diethyl ether

ORD record

ord-b355a776723a4d6080c41aa9ee2a0ea0

Source dataset

uspto-grants-1985_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04505922