Diethyl Ether → HCID 88235694, compound

Temperature

35 °C

A solution of 4-methylthiophenylacetic acid (10 grams, 54.8 mmol) and dimethylformamide (0.1 grams, 1.37 mmol) in methylene chloride (50 mL) at 35° C. was treated with thionyl chloride (4.4 mL, 60.25 mmol). The solution was maintained at 35° C. for 30 minutes, after which the solvent was removed by distillation at reduced pressure and replaced with fresh methylene chloride (50 mL). The acid chloride solution and ethylene (4.6 grams, 164 mmol) were introduced simultaneously over 25 minutes to a stirred mixture of aluminum bromide (36.5 grams, 137 mmol) in methylene chloride (450 mL) at -15 to -10° C. The resulting reaction mixture was stirred for 2.5 hours at -10 to 0° C. Water (200 mL) was slowly added (temperature≤25° C.) and the layers separated. The organic layer was washed successively with 5% sodium bicarbonate (200 mL) and brine (200 mL), dried over sodium sulfate and concentrated at reduced pressure to yield a dark-colored oil. The oil was dissolved in 3A alcohol (12 mL) and treated with a solution of sodium bisulfite (22.8 grams) in water (40 ML) and 3A alcohol (12 mL). After 30 minutes at 20° C. and 1 hour at 0° C., the precipitated bisulfite addition complex was filtered, washed with cold 3A alcohol (15 mL) and then ether (50 mL). The filtered solid was added to a mixture of ether (100 mL) and potassium carbonate (22.7 grams, 164 mmol), dissolved in water (75 mL), and stirred vigorously at 22° C. until the solid was completely dissolved. The organic layer was separated, washed with 1N hydrochloric acid (100 mL), then water (200 mL), dried over sodium sulfate and concentrated at reduced pressure to yield 5.8 grams (48%) of 6-methylthio-2-tetralone as a beige solid (high pressure liquid chromatography purity: 88%).

1. customafter which the solvent was removed by distillation at reduced pressure
2. customThe resulting reaction mixture
3. customthe layers separated
4. washThe organic layer was washed successively with 5% sodium bicarbonate (200 mL) and brine (200 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated at reduced pressure
7. customto yield a dark-colored oil
8. waitAfter 30 minutes at 20° C.
9. filtrationwas filtered
10. washwashed with cold 3A alcohol (15 mL)
11. stirringstirred vigorously at 22° C. until the solid
12. dissolutionwas completely dissolved
13. customThe organic layer was separated
14. washwashed with 1N hydrochloric acid (100 mL)
15. dry with materialwater (200 mL), dried over sodium sulfate
16. concentrationconcentrated at reduced pressure

ORD record

ord-56dc95d67d574c6dae2c17d1cba7baa0

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06111110