2-(chloromethoxy)-1,3-di(propan-2-yl)benzene

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

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

Procedure: 2,6-diisopropylphenol was treated with bromochloromethane in the presence of sodium hydroxide and THF to give an 85% yield of O-chloromethyl-2,6-diisopropylphenol, which was purified by vacuum distillation. Treatment of O-chloromethyl-2,6-diisopropylphenol with phosphoric acid and triethylamine in acetonitrile followed by solvent removal, dissolution in methanol, pH adjustment and precipitation with acetone gave an 85% yield of phosphono-O-methyl 2,6-diisopropylphenol disodium salt.

Conditions: temp:62.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser and thermometer. It was charged with 8.9 grams (0.05 moles) of 2,6-diisopropylphenol, 100 mL of THF and 4.0 grams (0.10 mole) of sodium hydroxide pellets. The resultant green suspension was heated to 60-65° C. and held for one hour. The reaction mixture was cooled to 30° C. and 100 mL (199 grams, 1.54 moles) bromochloromethane was added and heating was resumed. The reaction mixture was held at 64° C. for 2-3 hours until no more 2,6-diisopropylphenol was present as measured by GC. After cooling to 25° C., the suspension was filtered through Celite and the filter cake was washed with THF. The THF was removed by rotary evaporation and the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.) to give 9.6 grams (0.042 moles, 85% yield) of O-chloromethyl 2,6-diisopropyl phenol. A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser The reaction mixture was cooled to 30° C. heating After cooling to 25° C. the suspension was filtered through Celite the filter cake was washed with THF The THF was removed by rotary evaporation the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.)

Conditions: temp:62.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser and thermometer. It was charged with 8.9 grams (0.05 moles) of 2,6-diisopropylphenol, 100 mL of THF and 4.0 grams (0.10 mole) of sodium hydroxide pellets. The resultant green suspension was heated to 60-65° C. and held for one hour. The reaction mixture was cooled to 30° C. and 100 mL (199 grams, 1.54 moles) bromochloromethane was added and heating was resumed. The reaction mixture was held at 64° C. for 2-3 hours until no more 2,6-diisopropylphenol was present as measured by GC. After cooling to 25° C., the suspension was filtered through Celite and the filter cake was washed with THF. The THF was removed by rotary evaporation and the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.) to give 9.6 grams (0.042 moles, 85% yield) of O-chloromethyl 2,6-diisopropyl phenol. A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser The reaction mixture was cooled to 30° C. heating After cooling to 25° C. the suspension was filtered through Celite the filter cake was washed with THF The THF was removed by rotary evaporation the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.)

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Diisopropylphenol (20 kg, FW (formula weight)=178, 112 mol, 1 equiv.) is reacted with bromochloromethane (347 kg, FW=129, 2,682 mol, 24 equiv.) and sodium hydroxide (11 kg, FW=40, 280 mol, 2.5 equiv.) in tetrahydrofuran (108 kg, FW=72, 1,498 mol, 13.3 equiv.) at reflux for approximately 1.5 hours. After cooling to 20° C., the reaction mixture is quenched with water (87 kg). The organic layer is collected and washed with 15% sodium chloride aqueous solution (78 kg) twice. The organic layer is collected again after the layer separation, and the solvents are distilled from the organic layer to afford a crude oil. The crude oil is distilled by simple distillation to yield a purified chloromethyl(2,6-diisopropylphenyl)ether (FW=227) as a light yellow oil. at reflux for approximately 1.5 hours the reaction mixture is quenched with water (87 kg) The organic layer is collected washed with 15% sodium chloride aqueous solution (78 kg) twice The organic layer is collected again after the layer separation the solvents are distilled from the organic layer to afford a crude oil The crude oil is distilled by simple distillation

Conditions: temp:64.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser and thermometer. It was charged with 17.8 grams (0.10 moles) of 2,6-diisopropylphenol, 200 mL of THF, 8.0 grams (0.20 mole) of sodium hydroxide pellets, and 387 grams (3.0 moles, 194 mL) of bromochloromethane. The reaction mixture was heated to 64° C. and held for 2-3 hours until no more 2,6-diisopropylphenol was present as measured by GC. After cooling to 25° C., the suspension was filtered and the filter cake was washed with THF. The THF was removed by rotary evaporation and the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.) to give 16.9 grams (0.074 moles, 75% yield) of O-chloromethyl 2,6-diisopropyl phenol. A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser After cooling to 25° C. the suspension was filtered the filter cake was washed with THF The THF was removed by rotary evaporation the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.)

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

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

Procedure: 2,6-diisopropylphenol was treated with with bromochloromethane in the presence of sodium hydroxide and THF to give an 85% yield of O-chloromethyl-2,6-diisopropylphenol, which was purified by vacuum distillation. Treatment of O-chloromethyl-2,6-diisopropylphenol with phosphoric acid and triethylamine in acetonitrile followed by solvent removal, dissolution in methanol, pH adjustment and precipitation with acetone gave an 85% yield of phosphono-O-methyl 2,6-diisopropylphenol disodium salt.

Conditions: temp:62.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser and thermometer. It was charged with 8.9 grams (0.05 moles) of 2,6-diisopropylphenol, 100 mL of THF and 4.0 grams (0.10 mole) of sodium hydroxide pellets. The resultant green suspension was heated to 60-65° C. and held for one hour. The reaction mixture was cooled to 30° C. and 100 mL (199 grams, 1.54 moles) bromochloromethane was added and heating was resumed. The reaction mixture was held at 64° C. for 2-3 hours until no more 2,6-diisopropylphenol was present as measured by GC. After cooling to 25° C., the suspension was filtered through Celite and the filter cake was washed with THF. The THF was removed by rotary evaporation and the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.) to give 9.6 grams (0.042 moles, 85% yield) of O-chloromethyl 2,6-diisopropylphenol. A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser The reaction mixture was cooled to 30° C. heating After cooling to 25° C. the suspension was filtered through Celite the filter cake was washed with THF The THF was removed by rotary evaporation the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.)

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Diisopropylphenol (20 kg, FW (formula weight)=178, 112 mol, 1 equiv.) is reacted with bromochloromethane (347 kg, FW=129, 2,682 mol, 24 equiv.) and sodium hydroxide (11 kg, FW=40, 280 mol, 2.5 equiv.) in tetrahydrofuran (108 kg, FW=72, 1,498 mol, 13.3 equiv.) at reflux for approximately 1.5 hours. After cooling to 20° C., the reaction mixture is quenched with water (87 kg). The organic layer is collected and washed with 15% sodium chloride aqueous solution (78 kg) twice. The organic layer is collected again after the layer separation, and the solvents are distilled from the organic layer to afford a crude oil. The crude oil is distilled by simple distillation to yield a purified chloromethyl(2,6-diisopropylphenyl)ether (FW=227) as a light yellow oil. at reflux for approximately 1.5 hours the reaction mixture is quenched with water (87 kg) The organic layer is collected washed with 15% sodium chloride aqueous solution (78 kg) twice The organic layer is collected again after the layer separation the solvents are distilled from the organic layer to afford a crude oil The crude oil is distilled by simple distillation

Conditions: temp:64.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser and thermometer. It was charged with 17.8 grams (0.10 moles) of 2,6-diisopropylphenol, 200 mL of THF, 8.0 grams (0.20 mole) of sodium hydroxide pellets, and 387 grams (3.0 moles, 194 mL) of bromochloromethane. The reaction mixture was heated to 64° C. and held for 2-3 hours until no more 2,6-diisopropylphenol was present as measured by GC. After cooling to 25° C., the suspension was filtered and the filter cake was washed with THF. The THF was removed by rotary evaporation and the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.) to give 16.9 grams (0.074 moles, 75% yield) of O-chloromethyl 2,6-diisopropyl phenol. A four-necked 500 mL round bottom flask was equipped with a mechanical stirrer, nitrogen inlet, condenser After cooling to 25° C. the suspension was filtered the filter cake was washed with THF The THF was removed by rotary evaporation the resultant oil was distilled under vacuum (0-1 torr, b.p.=80° C.)

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

Procedure: 2,6-diisopropylphenol was treated with bromochloromethane in the presence of sodium hydroxide and THF to give an 85% yield of O-chloromethyl-2,6-diisopropylphenol, which was purified by vacuum distillation. Treatment of O-chloromethyl-2,6-diisopropylphenol with phosphoric acid and triethylamine in acetonitrile followed by solvent removal, dissolution in methanol, pH adjustment and precipitation with acetone gave an 85% yield of phosphono-O-methyl 2,6-diisopropylphenol disodium salt.