Hydrogen Bromide → HCID 14646171, compound

In a 2 liter, three-necked flask equipped with a reflux condenser and an addition funnel are placed 200 g pentaerythritol (1.47 mole) and 16 ml 48% hydrobromic acid in about 500 ml glacial acetic acid. The mixture is refluxed for about one-half hour until all pentaerythritol is dissolved. Then 170 ml 48% hydrobromic acid are added, followed by 310 ml acetic anhydride and the mixture is refluxed for 3 hours. Then, 94 ml 48% hydrobromic acid followed by 150 ml acetic anhydride are added and the mixture is refluxed for an additional 3 hours. The acetic acid is then removed as completely as possible on a rotary evaporator. Ethanol (95%, 750 ml) and 17 ml 48% hydrobromic acid are then added to the residue. The flask is equipped with 1 m Vigreux column and the azeotrope ethyl acetate/ethanol is slowly distilled off. When 500 ml distillate has been collected, an additional 750 ml 95% ethanol is added and the distillation is continued until about 400 ml is left over. After cooling, the precipitated pentaerythritol is filtered off. The solvent is evaporated and the residue is dissolved in water. The aqueous phase is extracted twice with carbon tetrachloride and twice with ether. The water is evaporated on the rotary evaporator and the last traces of water are removed by azeotropic distillation with toluene using a Dean-Stark trap. The solid is recrystalized from chloroform containing 10% acetonitrile. The first crop yielded 190 g monobromopentaerythritol. The total yield is 70%.

1. customIn a 2 liter, three-necked flask equipped with a reflux condenser and an addition funnel
2. dissolutionis dissolved
3. temperaturethe mixture is refluxed for 3 hours
4. additionare added
5. temperaturethe mixture is refluxed for an additional 3 hours
6. customThe acetic acid is then removed as completely as
7. custompossible on a rotary evaporator
8. additionEthanol (95%, 750 ml) and 17 ml 48% hydrobromic acid are then added to the residue
9. customThe flask is equipped with 1 m Vigreux column
10. distillationthe azeotrope ethyl acetate/ethanol is slowly distilled off
11. distillationWhen 500 ml distillate has been collected
12. additionan additional 750 ml 95% ethanol is added
13. distillationthe distillation
14. waitis left over
15. temperatureAfter cooling
16. filtrationthe precipitated pentaerythritol is filtered off
17. customThe solvent is evaporated
18. dissolutionthe residue is dissolved in water
19. extractionThe aqueous phase is extracted twice with carbon tetrachloride and twice with ether
20. customThe water is evaporated on the rotary evaporator
21. customthe last traces of water are removed by azeotropic distillation with toluene using a Dean-Stark trap
22. customThe solid is recrystalized from chloroform containing 10% acetonitrile

ORD record

ord-53cfb5cd73154716813a573e6099bd9d

Source dataset

uspto-grants-1985_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04526949