Hydrochloric Acid → 6-Bromo-1-hydroxy-2-hexanone

温度

10 °C

To 191.4 g of tris-trimethylsilyloxyethylene (Example 267) containing 15 drops of stannic tetrachloride under argon with stirring at 10° C. is added 87 g of 5-bromopentanoyl chloride (Example 274) dropwise. After one-half of the acid chloride is added, the mixture is stirred until an exotherm ensues. The remaining acid chloride is added dropwise maintaining the reaction exotherm at 65° C. The mixture is then stirred for 2.5 hours. The mixture is slowly poured into a stirred mixture of 100 ml of 0.6 N hydrochloric acid and 200 ml of tetrahydrofuran. The mixture is stirred for 30 minutes and poured into brine. The mixture is extracted with ether. The ether solution is washed with saturated sodium bicarbonate and dried over magnesium sulfate. The solvent is removed. The residue is mixed with petroleum ether and cooled in dry-ice-acetone to induce crystallization. The petroleum ether is decanted and the solid is dried at reduced pressure to give 54.72 g of the title compound.

1. stirringthe mixture is stirred until an exotherm ensues
2. temperaturemaintaining
3. customthe reaction exotherm at 65° C
4. stirringThe mixture is then stirred for 2.5 hours
5. stirringThe mixture is stirred for 30 minutes
6. extractionThe mixture is extracted with ether
7. washThe ether solution is washed with saturated sodium bicarbonate
8. dry with materialdried over magnesium sulfate
9. customThe solvent is removed
10. additionThe residue is mixed with petroleum ether
11. temperaturecooled in dry-ice-acetone
12. customcrystallization
13. customThe petroleum ether is decanted
14. customthe solid is dried at reduced pressure

ORDレコード

ord-688bd232f5834625a58e64564c8faae7

出典データセット

uspto-grants-1980_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04235797