Propargyl alcohol → 2,4-Heptadiyn-1-ol, 6,6-dimethyl-

Nitrogen was bubbled through a mixture of cupric chloride (154 mg), NH2OH.HCl (0.45 g), and 70% aqueous diethylamine (9 ml) in 11 ml of water and 23 ml of methanol, for a few minutes. Propargyl alcohol (3.8 g, 0.068 mol) was added with stirring under nitrogen whereupon a yellow precipitate formed immediately. The mixture was warmed to 35°-40° C. for 15 minutes and 1-bromo-2-t-butyl-acetylene (8.57 g, 0.053 mmol) was added over 15 minutes. The mixture was stirred at 35°-40° C. for 45 minutes, then at room temperature for 1 hour. Aqueous potassium cyanide (0.45 g in 45 ml of water) was added and the mixture was stirred for one minute. The mixture was poured into 50 ml of water and extracted 5 times with ether. The combined organic phase was washed with water and dried over magnesium sulfate. The solvents were removed and the residue was distilled under reduced pressure through a column packed with glass helices. 6,6-Dimethyl-2,4-heptadiyne-1-ol (3.63 grams) was collected at 85° C. and 0.5 mm of mercury.

1. customNitrogen was bubbled through a mixture of cupric chloride (154 mg), NH2OH.HCl (0.45 g), and 70% aqueous diethylamine (9 ml) in 11 ml of water and 23 ml of methanol, for a few minutes
2. customformed immediately
3. temperatureThe mixture was warmed to 35°-40° C. for 15 minutes
4. stirringThe mixture was stirred at 35°-40° C. for 45 minutes
5. stirringthe mixture was stirred for one minute
6. extractionextracted 5 times with ether
7. washThe combined organic phase was washed with water
8. dry with materialdried over magnesium sulfate
9. customThe solvents were removed
10. distillationthe residue was distilled under reduced pressure through a column
11. custom6,6-Dimethyl-2,4-heptadiyne-1-ol (3.63 grams) was collected at 85° C.

ORD record

ord-8aebcc3e6eff4e9db12589a2692ffb01

Source dataset

uspto-grants-1988_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04751245