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

Temperature

10 °C

To 191.4 g. of tris-trimethylsilyloxyethylene (Example 74) containing 15 drops of stannic tetrachloride under argon with stirring at 10° C. is added 87 g. of 5-bromopentanoyl chloride (Example 81) 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 0.6N 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 64.72 g. of the title compound.

1. additionis added 87 g
2. stirringthe mixture is stirred until an exotherm ensues
3. temperaturemaintaining
4. customthe reaction exotherm at 65° C
5. stirringThe mixture is then stirred for 2.5 hours
6. additionThe mixture is slowly poured into a stirred mixture of 100 ml
7. stirringThe mixture is stirred for 30 minutes
8. extractionThe mixture is extracted with ether
9. washThe ether solution is washed with saturated sodium bicarbonate
10. dry with materialdried over magnesium sulfate
11. customThe solvent is removed
12. additionThe residue is mixed with petroleum ether
13. temperaturecooled in dry ice acetone
14. customcrystallization
15. customThe petroleum ether is decanted
16. customthe solid is dried at reduced pressure
17. customto give 64.72 g

ORD record

ord-cc02ed86a38e48e09fb56fb719ed763c

Source dataset

uspto-grants-1981_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04254036