Hydrochloric Acid → HCID 11695119, compound

To a 1 L round bottom flask, equipped with a reflux condenser, was added 5-(4-Benzyloxy-phenoxy)-pentanoic acid ethyl ester (15.13 g, 46 mmol) and 2N aqueous sodium hydroxide (47 mL). The mixture was allowed to stir for 30 minutes. Water (200 mL) was added. The mixture was stirred for 20 minutes then heated to reflux for 2 hours to form a brown solution. The solution was quickly cooled to room temperature by the addition of ice. The cooled solution was acidified with 2N aqueous hydrochloric acid (50 mL) and the resulting white precipitate was collected by suction filtration, washed with water (2×100 mL), hexanes (2×100 mL), and dried under vacuum over night. The powder was finely ground and washed with hexanes (1×250 mL) and diethyl ether (1×250 mL) to yield a white powder. This powder was dissolved in a mixture of ethyl acetate (300 mL) and diethyl ether (200 mL) in a 1 L beaker. The solution was heated for 10 minutes, methanol (5 mL) added, heated an additional 10 minutes, and then filtered through a Celite plug to yield a clear yellow solution. The product was crystallized by slow addition of hexanes. The first crop of crystals was collected by filtration and hexanes (200 mL) was added to the mother liquor. The solution was then concentrated under reduced pressure to a volume of 400 mL and allowed to rest. The second batch of crystals was collected by filtration and combined with the first. The product (8.92 g, 65%) was isolated as a white crystalline material, mp 127-128° C. Combustion analysis: Found: C, 71.01; H, 6.98%; C18H20O4 requires C, 71.98; H, 6.71%;

1. customTo a 1 L round bottom flask, equipped with a reflux condenser
2. stirringThe mixture was stirred for 20 minutes
3. temperaturethen heated
4. temperatureto reflux for 2 hours
5. customto form a brown solution
6. filtrationthe resulting white precipitate was collected by suction filtration
7. washwashed with water (2×100 mL), hexanes (2×100 mL)
8. customdried under vacuum over night
9. washwashed with hexanes (1×250 mL) and diethyl ether (1×250 mL)
10. customto yield a white powder
11. temperatureThe solution was heated for 10 minutes
12. temperatureheated an additional 10 minutes
13. filtrationfiltered through a Celite plug
14. customto yield a clear yellow solution
15. customThe product was crystallized by slow addition of hexanes
16. filtrationThe first crop of crystals was collected by filtration and hexanes (200 mL)
17. additionwas added to the mother liquor
18. concentrationThe solution was then concentrated under reduced pressure to a volume of 400 mL
19. filtrationThe second batch of crystals was collected by filtration

ORD record

ord-235ba5c8cc8d416b93f42e6a5aad80d7

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273794B2