Sodium Hydroxide → HCID 86703816, Verbindung

A 10 mL round bottom flask equipped with a stir bar was charged with 3,7-dimethyloxepan-2-one (61, 0.729 g, 5.13 mmol), hydroiodic acid (2.029 ml, 15.38 mmol) and thiourea (2.73 g, 35.91 mmol). The flask was equipped with a water cooled water condenser, placed under a nitrogen atmosphere and heated to reflux. The reaction proceeded at reflux overnight. A sodium hydroxide (3.69 g, 92 mmol) solution in water (5 mL) was then added to the reaction flask. The reaction was refluxed overnight. The reaction mixture was removed from heat, cooled to room temperature and the flask contents were transferred to a separatory funnel. The aqueous layer was extracted with ethyl acetate and the extract was set to the side. The aqueous layer was acidified with HCl to pH 2 and extracted with ethyl acetate (2×100 mL) and methylene chloride (1×100 mL). The organic extracts were combined, washed with 30 mL of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 823 mg of crude 6-mercapto-2-methylheptanoic acid (62, 92% yield) as a light brown oil.

1. customA 10 mL round bottom flask equipped with a stir bar
2. temperaturecooled water condenser
3. temperatureheated to reflux
4. temperatureat reflux overnight
5. temperatureThe reaction was refluxed overnight
6. customThe reaction mixture was removed
7. temperaturefrom heat
8. customthe flask contents were transferred to a separatory funnel
9. extractionThe aqueous layer was extracted with ethyl acetate
10. extractionextracted with ethyl acetate (2×100 mL) and methylene chloride (1×100 mL)
11. washwashed with 30 mL of brine
12. dry with materialdried over anhydrous sodium sulfate
13. concentrationconcentrated in vacuo

ORD-Eintrag

ord-7d37663ff0ec4b88b15bf26d1291946d

Quelldatensatz

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09090629B2