Carbon Tetrachloride → 2-Chloro-4-(2,2,2-trichloro-1-hydroxyethyl)phenol

3-Chloro-4-hydroxy benzaldehyde (15.6 g, 0.1 mol) was added to 200 ml of dimethylformamide, a mixture was stirred, aluminium (8.09 g, 0.3 mol) and leadbromide (3.67 g, 0.01 mmol) were added thereto. CCl4 (61.53 g, 0.4 mol) was slowly added to the reaction mixture. The mixture was stirred at room temperature for 10 hours, and unreacted solid was filtered to remove therefrom. After sequentially adding 5% HCl, ethylacetate and water thereto, the mixture was extracted three times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and distilled. The resulting residue was subjected to column chromatography (ethyl acetate: n-hexane=1:4) to obtain the title compound (24.55 g, 89%).

1. stirringThe mixture was stirred at room temperature for 10 hours
2. filtrationunreacted solid was filtered
3. customto remove
4. additionAfter sequentially adding 5% HCl, ethylacetate and water
5. extractionthe mixture was extracted three times with ethyl acetate
6. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. distillationdistilled

ORD record

ord-bbfe5d8c1663410d980d4f9bb4042176

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410302B2