Allyl bromide → HCID 21996721, compound

Into a 500 mL round bottom flask equipped with an overhead stirrer, thermometer and a nitrogen inlet were placed 56.085 g (0.5 mol) of distilled 1,2,3,6-tetrahydrobenzylalcohol, 90.75 g (0.75 mol) of allyl bromide, 100 mL of toluene and 30 g (0.75 mol) of sodium hydroxide. The reaction mixture was stirred at room temperature for 15 minutes. Then, 3 g (0.01 mol) of tetra-n-butylammonium bromide was added and the reaction mixture slowly heated to reflux (65° C.) and maintained at that temperature for eight hours. The reaction mixture was cooled and filtered to remove the sodium bromide which precipitated during the reaction. The filtrate was poured into 500 mL of distilled water, the organic layers were separated and the aqueous layer extracted with fresh toluene. The combined organic layers were washed with three 200 mL portions of distilled water and the organic phase was dried over anhydrous sodium sulfate. Then, the excess allyl bromide and toluene were removed using a rotary evaporator and the reaction mixture subjected to vacuum distillation. The clear liquid distillate amounted to 62.32 g (82% recovered yield). Fractional vacuum distillation gave pure CA with a boiling point of 22° C. at 0.05 mm Hg.

1. customInto a 500 mL round bottom flask equipped with an overhead stirrer
2. customthermometer and a nitrogen inlet were placed
3. temperaturethe reaction mixture slowly heated
4. temperatureto reflux (65° C.)
5. temperaturemaintained at that temperature for eight hours
6. temperatureThe reaction mixture was cooled
7. filtrationfiltered
8. customto remove the sodium bromide which
9. customprecipitated during the reaction
10. additionThe filtrate was poured into 500 mL of distilled water
11. customthe organic layers were separated
12. extractionthe aqueous layer extracted with fresh toluene
13. washThe combined organic layers were washed with three 200 mL portions of distilled water
14. dry with materialthe organic phase was dried over anhydrous sodium sulfate
15. customThen, the excess allyl bromide and toluene were removed
16. customa rotary evaporator
17. distillationthe reaction mixture subjected to vacuum distillation
18. distillationThe clear liquid distillate amounted to 62.32 g (82% recovered yield)
19. distillationFractional vacuum distillation
20. customgave pure CA with a boiling point of 22° C. at 0.05 mm Hg

ORD record

ord-3f8abe01e1154dba8cae6b1567663fdc

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06075155