2,2,6,6-tetrachlorocyclohexan-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a blanket of nitrogen were mixed 2,2,6,6-tetrachlorocyclohexanone (100 parts), sodium acetate (424 parts) and water (1,059 parts), and the mixture refluxed for 10 minutes. The mixture was then cooled to 50° C. when sodium bicarbonate (318 parts) was added giving severe foaming. The mixture was then extracted continuously with ether, the extract dried over magnesium sulphate and evaporated to give a residue (39 parts). The residue was triturated with chloroform (39 parts) to give after filtering and drying in air 15.2 parts of pyrogallol (28.5% yield) as a tan solid, m.pt. 130.5°-133.5° C. the mixture refluxed for 10 minutes was added giving severe foaming The mixture was then extracted continuously with ether the extract dried over magnesium sulphate evaporated to give a residue (39 parts) The residue was triturated with chloroform (39 parts) to give after filtering

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a blanket of nitrogen were mixed 2,2,6,6-tetrachlorocyclohexanone (100 parts), sodium acetate (424 parts) and water (1,059 parts), and the mixture refluxed for 10 minutes. The mixture was then cooled to 50° C. when sodium bicarbonate (318 parts) was added giving severe foaming. The mixture was then extracted continuously with ether, the extract dried over magnesium sulphate and evaporated to give a residue (39 parts). The residue was triturated with chloroform (39 parts) to give after filtering and drying in air 15.2 parts of pyrogallol (28.5% yield) as a tan solid, m.pt. 130.5°-133.5° C. the mixture refluxed for 10 minutes was added giving severe foaming The mixture was then extracted continuously with ether the extract dried over magnesium sulphate evaporated to give a residue (39 parts) The residue was triturated with chloroform (39 parts) to give after filtering

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a blanket of nitrogen were mixed 2,2,6,6-tetrachlorocyclohexanone (100 parts), sodium acetate (424 parts) and water (1,059 parts), and the mixture refluxed for 10 minutes. The mixture was then cooled to 50° C. when sodium bicarbonate (318 parts) was added giving severe foaming. The mixture was then extracted continuously with ether, the extract dried over magnesium sulphate and evaporated to give a residue (39 parts). The residue was triturated with chloroform (39 parts ) to give after filtering and drying in air 15.2 parts of pyrogallol (28.5% yield) as a tan solid, m.pt. 130.5°-133.5° C. the mixture refluxed for 10 minutes was added giving severe foaming The mixture was then extracted continuously with ether the extract dried over magnesium sulphate evaporated to give a residue (39 parts) The residue was triturated with chloroform (39 parts ) to give after filtering

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 118 g (0.5 mol) of 2,2,6,6-tetrachlorocyclohexanone and 1 g (0.006 mol) of hexamethylphosphorotriamide were introduced into the reactor used in Example 1. The reaction mixture was heated at 150°-180° C., under stirring; the reaction was terminated when the evolution of hydrogen chloride from the reaction mixture ceased. The reaction mixture was then distilled under reduced pressure (boiling point (20 mm Hg)=100° C.) to yield 52 g of 2,6-dichlorophenol. The reaction mixture was heated at 150°-180° C. the reaction was terminated when the evolution of hydrogen chloride from the reaction mixture The reaction mixture was then distilled under reduced pressure (boiling point (20 mm Hg)=100° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 190 g (0.8 mol) of 2,2,6,6-tetrachlorocyclohexanone and 3 g (0.065 mol) of triphenylarsine were introduced into the reactor used in Example 1. The reaction mixture was heated at 150°-180° C., under stirring. Same was then treated as in Example 1 to yield 103.4 g of 2,6-dichlorophenol. The reaction mixture was heated at 150°-180° C. Same was then treated as in Example 1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 236 g (1 mol) of 2,2,6,6-tetrachlorocyclohexanone and 2.5 g (0.01 mol) of triphenylphosphine were introduced into a reactor equipped with a stirrer and a condenser. The mixture was heated at 150°-180° C. under stirring; the reaction was terminated when the evolution of hydrogen chloride from the reaction mixture ceased. The reaction mixture was then distilled under reduced pressure (boiling point (20 mm Hg)=100° C.) to yield 137.5 g of 2,6-dichlorophenol. equipped with a stirrer and a condenser The mixture was heated at 150°-180° C. the reaction was terminated when the evolution of hydrogen chloride from the reaction mixture The reaction mixture was then distilled under reduced pressure (boiling point (20 mm Hg)=100° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure of Example 1 was repeated except that 1.56 moles of each amine and ammonia shown in Table 1 was used instead of aniline to give oily 2,2,6,6-tetrachlorocyclohexaneimine derivative. In Examples 4 and 5, gaseous ammonia and methylamine were introduced into the mixture of 2,2,6,6-tetrachlorocyclohexanone, toluene and titanium tetrachloride, respectively. The structural formulae, yields and results of IR analysis of the obtained 2,2,6,6-tetrachlorocyclohexaneimine derivatives (I) are shown in Table 1. The structural formulae, yields