Methyl Benzoate → 85081-69-2

(E)-cyclooct-4-enol was synthesized from (Z)-cyclooct-4-enol using a modification of a previously reported protocol (Royzen, M. et al. J. Am. Chem. Soc. 2008, 130, 3760-3761). Briefly, 1 gram of cyclooctenol (2) and 1.1 g methyl benzoate sensitizer was added to 250 mL solvent (9:1 Ether:Hexanes) in a 500 mL quartz reaction vessel (Southern New England Ultraviolet Company). No attempt to degas the solution was made. The vessel was irradiated with 254 nm light in a Rayonet RPR-100 UV reactor (Southern New England Ultraviolet Company) under constant stirring. At 30 minute intervals, the irradiation was stopped and the entire solution was passed through a column packed with silver nitrate (10%) impregnated silica (commercially available from Aldrich). The solution that passes through was then transferred back into the quartz flask and irradiation was continued. After 6 hours the irradiation was stopped and the silica was added to a solution of ammonium hydroxide and stirred for 5 minutes after which ether was added and stirring continued for 5 more minutes. After stirring the ether phase was decanted, washed with water, dried with magnesium sulfate, and evaporated yielding trans-cyclooctenol (40%) as a mixture of isomers as previously reported. The isomers were separated by column chromatography (1:1 Ethyl Acetate Hexanes) and verified by proton NMR using the previously reported proton NMR spectra (Royzen, M. et al. J. Am. Chem. Soc. 2008, 130, 3760-3761) The major isomer (more polar isomer) was used for the synthesis of (E)-cyclooct-4-enyl 2,5-dioxopyrrolidin-1-yl carbonate.

1. customNo attempt to degas the solution
2. customThe vessel was irradiated with 254 nm light in a Rayonet RPR-100 UV reactor (Southern New England Ultraviolet Company) under constant stirring
3. customthe irradiation
4. customthrough was then transferred back into the quartz flask and irradiation
5. customAfter 6 hours the irradiation
6. additionthe silica was added to a solution of ammonium hydroxide
7. additionwas added
8. stirringstirring
9. stirringAfter stirring the ether phase
10. customwas decanted
11. washwashed with water
12. dry with materialdried with magnesium sulfate
13. customevaporated

ORD record

ord-39cfb185ca4146af97d98ec9edf4c44c

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08900549B2