Cyclohexanol → HCID 53700903, compound

8 g (56.3 mmol) of 5-methyl-1,2,4-oxadiazol-3-yl-acetic acid were suspended in 8 g (80 mmol) of re-distilled, dry cyclohexanol and 8 g (52.2 mmol) of phosphorous oxychloride were added dropwise under anhydrous conditions over about 7 minutes to the mixture. During the addition, the mixture was heated on a steam bath and heating was continued for 45 minutes. After the reaction mixture had cooled to room temperature, 75 ml of ice-water and 50 ml of diethyl ether were added and the mixture was stirred until a clear two-layer system was obtained. The flask was placed in an ice-salt bath and solid potassium hydroxide was added until a pH of 10.5 was reached. The layers were separated and the aqueous layer was extracted three times with 40 ml portions of diethyl ether. The four ethereal extracts were combined, washed once with a small volume of ice-water and subsequently concentrated in vacuo. The 10 g of residue was distilled in vacuo to obtain 7.9 g (62% yield) of cyclohexyl 5-methyl-1,2,4-oxadiazol-3-yl-acetate with a b.p. of 120°-121° C. at 0.9-1.0 mm and a refractive index nD25 =1.4715.

1. distillationof re-distilled
2. additionDuring the addition
3. temperaturethe mixture was heated on a steam bath
4. temperatureheating
5. customwas obtained
6. customThe flask was placed in an ice-salt bath
7. customThe layers were separated
8. extractionthe aqueous layer was extracted three times with 40 ml portions of diethyl ether
9. washwashed once with a small volume of ice-water
10. concentrationsubsequently concentrated in vacuo
11. distillationThe 10 g of residue was distilled in vacuo

ORD record

ord-1697d700571d481abd44495b02aa18c3

Source dataset

uspto-grants-1979_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04160829