Tetrahydrofuran → HCID 22457346, compound

Temperature

5 °C

4-Vinylphenylacetic acid 34 (8.15 g, 50.3 mmol) was placed in a three-neck round bottom flask attached with a thermometer, and an addition funnel with a drying tube. Tetrahydrofuran (80 mL, distilled over Na/K alloy) was added to the reaction flask, and the solution was cooled with an ice bath. Trifluoroacetic anhydride (15 mL, 106.2 mmol) was slowly added using an addition funnel so that the reaction temperature was kept below 10° C. The solution was allowed to stir at 5° C. for 2 h. A solution of 2-Methylpropanol (freshly distilled over CaH2, 36 mL, 376 mmol) in THF (50 mL) was added dropwise keeping the reaction temperature below 10° C. The solution was stirred for an additional 2 hours at 5° C., and then overnight at room temperature. Ethyl ether (200 mL) was added to the solution, and 170 mL of 1.25 N aqueous NaOH was slowly added while cooling with an ice bath. The solution was then allowed to stir at room temperature for 2 h. The organic layer was separated, washed with water until neutral, washed with brine, and then dried over anhydrous MgSO4. The solvents were removed in vacuo, and 9.85 g of clear liquid was obtained in 90% yield.

1. customattached with a thermometer, and an addition funnel with a drying tube
2. temperaturethe solution was cooled with an ice bath
3. customwas kept below 10° C
4. distillationA solution of 2-Methylpropanol (freshly distilled over CaH2, 36 mL, 376 mmol) in THF (50 mL)
5. additionwas added dropwise
6. customthe reaction temperature below 10° C
7. stirringThe solution was stirred for an additional 2 hours at 5° C.
8. customovernight
9. customat room temperature
10. additionEthyl ether (200 mL) was added to the solution, and 170 mL of 1.25 N aqueous NaOH
11. additionwas slowly added
12. temperaturewhile cooling with an ice bath
13. stirringto stir at room temperature for 2 h
14. customThe organic layer was separated
15. washwashed with water until neutral,
16. washwashed with brine
17. dry with materialdried over anhydrous MgSO4
18. customThe solvents were removed in vacuo

ORD record

ord-558b45a8a4f341098a492c85e7fbc658

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06399273B1