1-(2-Chloro-6-hydroxyphenyl)ethanone Chemical Properties

Boiling point:

225.4±20.0 °C(Predicted)

Density 

1.298±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

9.20±0.10(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C8H7ClO2/c1-5(10)8-6(9)3-2-4-7(8)11/h2-4,11H,1H3

InChIKey

RUSSVKYJPIADHS-UHFFFAOYSA-N

SMILES

C(=O)(C1=C(O)C=CC=C1Cl)C

Safety Information

HS Code 

2914500090

1-(2-Chloro-6-hydroxyphenyl)ethanone Usage And Synthesis

Uses

1-(2-Chloro-6-hydroxyphenyl)ethanone is used for synthesis and structure-activity relationship of novel spiropiperidine-based stearoyl-CoA desaturase-1 inhibitors.

Preparation

Preparation by diazotization of 2-amino-6-chloro-acetophenone, followed by hydrolysis of the obtained diazonium salt (55%).

Synthesis

1. To a solution of 2-chloro-6-hydroxybenzonitrile (614 mg, 4 mmol) in tetrahydrofuran (THF, 10 mL) under argon protection is slowly added a solution of methylmagnesium bromide in toluene/THF (3:1, 1.4 M, 6.4 mL, 9 mmol). Note: Gas escapes during the reaction. 2. Stir the reaction mixture at room temperature until the escape of gas ceases. 3. Transfer the reaction mixture to a sealed tube and stir overnight at 65°C. 4. 4. upon completion of the reaction, the reaction is quenched with water and acidified with aqueous hydrochloric acid. 5. The organic layer containing 1-(2-chloro-6-hydroxyphenyl)ethanone was extracted with dichloromethane (DCM). 6. The product was purified by column chromatography using dichloromethane/hexane (1:1) as eluent to afford 1-(2-chloro-6-hydroxyphenyl)ethanone (100 mg, 15% yield).

References

[1] Patent: WO2010/56631, 2010, A1. Location in patent: Page/Page column 132-134