Ethylbenzene → (5-Chloro-2-hydroxyphenyl)(4-ethylphenyl)methanone

Temperature

-5 °C

A solution of 2-methoxy-5-chlorobenzoic acid (2.0 g, 10.5 mmol) in dry CH2Cl2 (10 mL) was stirred at room temperature under agron. Oxalyl chloride (2.0 g, 15.8 mmol) was added dropwise to the reaction mixture followed by DMF (0.04 mL). After stirring overnight, the volatiles were evaporated using a rotary evaporator and the residue was dissolved in dry CH2Cl2 (10 mL) at room temperature under agron. After cooling to −5° C., ethylbenzene (2.57 mL, 21 mmol) was added, followed by portionwise addition of AlCl3 (2.80 g, 21 mmol) while maintaining the reaction temperature between −5° C. and 0° C. The reaction mixture was stirred for 4 h at room temperature, and then poured into ice water and extracted with CH2Cl2 (50 mL×2). The organic layer was then washed with 1N HCl (50 mL), 1N NaOH (50 mL), water (50 mL) and brine (50 mL) and dried over anhydrous Na2SO4. The filtrate was concentrated and the crude product was purified by column chromatography (PE:EA=10:1) to give the target compound (1.944 g).

1. customthe volatiles were evaporated
2. customa rotary evaporator
3. dissolutionthe residue was dissolved in dry CH2Cl2 (10 mL) at room temperature under agron
4. temperaturewhile maintaining the reaction temperature between −5° C. and 0° C
5. stirringThe reaction mixture was stirred for 4 h at room temperature
6. extractionextracted with CH2Cl2 (50 mL×2)
7. washThe organic layer was then washed with 1N HCl (50 mL), 1N NaOH (50 mL), water (50 mL) and brine (50 mL)
8. dry with materialdried over anhydrous Na2SO4
9. concentrationThe filtrate was concentrated
10. customthe crude product was purified by column chromatography (PE:EA=10:1)

ORD record

ord-42bee6de9b444d489f1e075ac4ea2956

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129434B2