Methanol → HCID 15078772, compound

A solution of neopentyl alcohol (600 g, 6.82 moles) and toluene (1200 mL) was refluxed in suspension with 1,2-dihydroxy-1-cyclobutene-3,4-dione (230 g, 2.02 moles). Water was collected from the stirred mixture with a Dean-Stark separator. After water collection had stopped (ca. 11.5 hours) a clear, orange, homogeneous solution resulted. Reflux was continued and toluene (700 mL) was collected over an additional 1.5 hours. The solution was removed from reflux at this point and cooled to room temperature. Triethylamine (255 g, 2.50 moles) was added in a single portion to the stirred, room temperature solution. To this was added over 0.5 hour, a solution of bromopropylamine hydrobromide in absolute methanol (438 g, 2.0 moles of amine salt in 600 mL methanol). After addition was complete, the solution was stirred for an additional 0.5 hour. The mixture was concentrated at reduced pressure (45° C.) to a total volume of about 1500 mL. Water (2000 mL) was added and the solution was again concentrated at reduced pressure until about 1500 mL of distillate had been removed. The thick solution was filtered to isolate a white solid. The solid was recrystallized from 800 mL of warm isopropanol with gradual cooling to room temperature and -5° C. The product was collected by filtration, washed with two separate 500 mL portions of 1:1 hexane:isopropanol and dried at 45° C., aspirator pressure to a constant weight. The title compound was obtained as a white to very pale yellow powder, m.p. 111°-113° C., yield 528.4 g (86%).

1. customWater was collected from the stirred mixture with a Dean-Stark separator
2. customAfter water collection
3. custom(ca. 11.5 hours)
4. customresulted
5. temperatureReflux
6. customtoluene (700 mL) was collected over an additional 1.5 hours
7. customThe solution was removed
8. temperaturefrom reflux at this point
9. additionTo this was added over 0.5 hour
10. additionAfter addition
11. concentrationThe mixture was concentrated at reduced pressure (45° C.) to a total volume of about 1500 mL
12. additionWater (2000 mL) was added
13. concentrationthe solution was again concentrated at reduced pressure until about 1500 mL of distillate
14. customhad been removed
15. filtrationThe thick solution was filtered
16. customto isolate a white solid
17. customThe solid was recrystallized from 800 mL of warm isopropanol
18. temperaturewith gradual cooling to room temperature and -5° C
19. filtrationThe product was collected by filtration
20. washwashed with two
21. customseparate 500 mL portions of 1:1 hexane
22. dry with materialisopropanol and dried at 45° C.

ORD record

ord-3286a921737c45a09a5a89f8e01c459c

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04927970