Water → HCID 23013768, compound

Potassium carbonate (21.3 g, 154 mmol) was added to a solution of 2-chloro-6-cyclopropylphenyl acetate (16.3 g, 77 mmol) in methanol (80 ml) at once and the mixture was stirred at room temperature for 90 minutes. After water (240 ml) was added to the reaction mixture, the resulting mixture was concentrated by an evaporator to remove most of methanol. The obtained mixture was cooled to 0° C. and 4M hydrochloric acid was added thereto to make pH to 2 or lower such that the temperature of the mixture did not exceed 25° C. This was extracted with a 10% ethyl acetate-90% hexane (V/V) solvent mixture. The organic layer was combined and washed with a saturated aqueous NaCl solution, followed by drying with anhydrous sodium sulfate (90 g). After the solid was removed by filtration, the filtrate was concentrated to obtain a pale brown oil. This oil was purified by silica gel column chromatography (use of 120 g of Wakogel C-100E) to obtain 10.1 g of 2-chloro-6-cyclopropylphenol.

1. concentrationthe resulting mixture was concentrated by an evaporator
2. customto remove most of methanol
3. temperatureThe obtained mixture was cooled to 0° C.
4. addition4M hydrochloric acid was added
5. customdid not exceed 25° C
6. extractionThis was extracted with a 10% ethyl acetate-90% hexane (V/V) solvent mixture
7. washwashed with a saturated aqueous NaCl solution
8. dry with materialby drying with anhydrous sodium sulfate (90 g)
9. customAfter the solid was removed by filtration
10. concentrationthe filtrate was concentrated
11. customto obtain a pale brown oil
12. customThis oil was purified by silica gel column chromatography (use of 120 g of Wakogel C-100E)

ORD record

ord-def88169e02c4fd987236b50eb58e986

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07629494B2