sodium;octyl sulfate

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-Methyl-1-(propoxyethoxycarbonylmethyl)imidazolium bromide (3.32 g, 12.0 mmol) in distilled water (20 mL) was added in one portion sodium octyl sulfate (2.09 g, 9.00 mmol) and stirred at 60° C. for 2 h. The water was then slowly removed under vacuum. The precipitate was dissolved in DCM (10 mL) and washed with distilled water (2×5 mL). The product remaining was dried on the rotary evaporator and then under high vacuum for 8 h to yield a dark yellow grease at RT in 85% yield (3.33 g, 7.64 mmol). 1H δ ppm 9.45 (s, 1H), 7.48 (t, J=1.6 Hz, 1H), 7.41 (t, J=1.6 Hz, 1H), 5.25 (5, 2H), 4.36 (t, J=4.8 Hz, 2H), 4.01 (s, 3H), 3.67 (t, J=4.6 Hz, 2H), 3.43 (t, J=6.8 Hz, 2H), 1.63-1.58 (m, 2H), 0.92-0.86 (m, 3H) 13C δ ppm 166.45, 138.89, 123.71, 123.06, 73.04, 67, 92, 67.89, 65.67, 49.91, 36.58, 31.83, 29.50, 29.36, 29.26, 25.87, 22.73, 22.66, 14.13, 10.47 The water was then slowly removed under vacuum The precipitate was dissolved in DCM (10 mL) washed with distilled water (2×5 mL) The product remaining was dried on the rotary evaporator under high vacuum for 8 h to yield a dark yellow grease at RT in 85% yield (3.33 g, 7.64 mmol)

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

Procedure: 64.0 g of 35% sodium octyl sulfate (Aldrich, Milwaukee, Mich.) in water was slowly added in 31.0 g of 2-methoxy-4-(phenylamino)-benzenediazonium bisulfate (Diverstec, Fort Collins, Colo.) in 500 ml of water while stirring. The mixture was stored in dark at 0-5° C. for 5 hours. After decanting water, the resulting oil material was dissolved in 200 ml ethyl acetate. The solution was washed with 50 ml of 5% NaHCO3 and then with 50 ml of water. The organic layer was dried over anhydrous MgSO4 for 6 hours, and the solvent was removed by vacuum. 35.1 g of oil material was obtained. dark at 0-5° C. for 5 hours After decanting water the resulting oil material was dissolved in 200 ml ethyl acetate The solution was washed with 50 ml of 5% NaHCO3 The organic layer was dried over anhydrous MgSO4 for 6 hours the solvent was removed by vacuum

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

Procedure: 84.55 g (0.484 mole) of 1-butyl-3-methylimidazolium chloride (BMIM Cl) and 101.1 g (minimum 0.379 mole) of sodium octyl sulfate (technical grade; content≧87%) are dissolved in 200 ml of hot water. The water is slowly removed under vacuum. The solid formed is filtered off after dissolving the batch in methylene chloride. The filtrate is washed until the aqueous phase is colourless and free from chloride. The organic phase is dried over Na2SO4. Concentrating and drying under a high vacuum gives 111.0 g (0.319 mmole; 73% of the theoretical yield, based on sodium octyl sulfate) of an oily yellow liquid. The water is slowly removed under vacuum The solid formed is filtered off after dissolving the batch in methylene chloride The filtrate is washed until the aqueous phase The organic phase is dried over Na2SO4 Concentrating drying under a high vacuum gives 111.0 g (0.319 mmole

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-Methyl-1-(propoxyethoxycarbonylmethyl)imidazolium bromide (3.32 g, 12.0 mmol) in distilled water (20 mL) was added in one portion sodium octyl sulfate (2.09 g, 9.00 mmol) and stirred at 60° C. for 2 h. The water was then slowly removed under vacuum. The precipitate was dissolved in DCM (10 mL) and washed with distilled water (2×5 mL). The product remaining was dried on the rotary evaporator and then under high vacuum for 8 h to yield a dark yellow grease at RT in 85% yield (3.33 g, 7.64 mmol). 1H δ ppm 9.45 (s, 1H), 7.48 (t, J=1.6 Hz, 1H), 7.41 (t, J=1.6 Hz, 1H), 5.25 (5, 2H), 4.36 (t, J=4.8 Hz, 2H), 4.01 (s, 3H), 3.67 (t, J=4.6 Hz, 2H), 3.43 (t, J=6.8 Hz, 2H), 1.63-1.58 (m, 2H), 0.92-0.86 (m, 3H) 13C δ ppm 166.45, 138.89, 123.71, 123.06, 73.04, 67, 92, 67.89, 65.67, 49.91, 36.58, 31.83, 29.50, 29.36, 29.26, 25.87, 22.73, 22.66, 14.13, 10.47 The water was then slowly removed under vacuum The precipitate was dissolved in DCM (10 mL) washed with distilled water (2×5 mL) The product remaining was dried on the rotary evaporator under high vacuum for 8 h to yield a dark yellow grease at RT in 85% yield (3.33 g, 7.64 mmol)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-Methyl-1-(propoxyethoxycarbonylmethyl)imidazolium bromide (3.32 g, 12.0 mmol) in distilled water (20 mL) was added in one portion sodium octyl sulfate (2.09 g, 9.00 mmol) and stirred at 60° C. for 2 h. The water was then slowly removed under vacuum. The precipitate was dissolved in DCM (10 mL) and washed with distilled water (2×5 mL). The product remaining was dried on the rotary evaporator and then under high vacuum for 8 h to yield a dark yellow grease at RT in 85% yield (3.33 g, 7.64 mmol). 1H δ ppm 9.45 (s, 1H), 7.48 (t, J=1.6 Hz, 1H), 7.41 (t, J=1.6 Hz, 1H), 5.25 (5, 2H), 4.36 (t, J=4.8 Hz, 2H), 4.01 (s, 3H), 3.67 (t, J=4.6 Hz, 2H), 3.43 (t, J=6.8 Hz, 2H), 1.63-1.58 (m, 2H), 0.92-0.86 (m, 3H) 13C δ ppm 166.45, 138.89, 123.71, 123.06, 73.04, 67, 92, 67.89, 65.67, 49.91, 36.58, 31.83, 29.50, 29.36, 29.26, 25.87, 22.73, 22.66, 14.13, 10.47 The water was then slowly removed under vacuum The precipitate was dissolved in DCM (10 mL) washed with distilled water (2×5 mL) The product remaining was dried on the rotary evaporator under high vacuum for 8 h to yield a dark yellow grease at RT in 85% yield (3.33 g, 7.64 mmol)

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

Procedure: 84.55 g (0.484 mole) of 1-butyl-3-methylimidazolium chloride (BMIM Cl) and 101.1 g (minimum 0.379 mole) of sodium octyl sulfate (technical grade; content ≧87%) are dissolved in 200 ml of hot water. The water is slowly removed under vacuum. The solid formed is filtered off after dissolving the batch in methylene chloride. The filtrate is washed until the aqueous phase is colourless and free from chloride. The organic phase is dried over Na2SO4. Concentrating and drying under a high vacuum gives 111.0 g (0.319 mmole; 73% of the theoretical yield, based on sodium octyl sulfate) of an oily yellow liquid. The water is slowly removed under vacuum The solid formed is filtered off after dissolving the batch in methylene chloride The filtrate is washed until the aqueous phase The organic phase is dried over Na2SO4 Concentrating drying under a high vacuum gives 111.0 g (0.319 mmole

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

Procedure: 64.0 g of 35% sodium octyl sulfate (Aldrich, Milwaukee, Mich.) in water was slowly added in 31.0 g of 2-methoxy-4-(phenylamino)-benzenediazonium bisulfate (Diverstec, Fort Collins, Colo.) in 500 ml of water while stirring. The mixture was stored in dark at 0-5° C. for 5 hours. After decanting water, the resulting oil material was dissolved in 200 ml ethyl acetate. The solution was washed with 50 ml of 5% NaHCO3 and then with 50 ml of water. The organic layer was dried over anhydrous MgSO4 for 6 hours, and the solvent was removed by vacuum. 35.1 g of oil material was obtained. dark at 0-5° C. for 5 hours After decanting water the resulting oil material was dissolved in 200 ml ethyl acetate The solution was washed with 50 ml of 5% NaHCO3 The organic layer was dried over anhydrous MgSO4 for 6 hours the solvent was removed by vacuum

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

Procedure: 84.55 g (0.484 mole) of 1-butyl-3-methylimidazolium chloride (BMIM Cl) and 101.1 g (minimum 0.379 mole) of sodium octyl sulfate (technical grade; content≧87%) are dissolved in 200 ml of hot water. The water is slowly removed under vacuum. The solid formed is filtered off after dissolving the batch in methylene chloride. The filtrate is washed until the aqueous phase is colourless and free from chloride. The organic phase is dried over Na2SO4. Concentrating and drying under a high vacuum gives 111.0 g (0.319 mmole; 73% of the theoretical yield, based on sodium octyl sulfate) of an oily yellow liquid. The water is slowly removed under vacuum The solid formed is filtered off after dissolving the batch in methylene chloride The filtrate is washed until the aqueous phase The organic phase is dried over Na2SO4 Concentrating drying under a high vacuum gives 111.0 g (0.319 mmole