2-(2-ethylhexoxymethyl)oxirane

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

Procedure: In a 250 mL, round bottom 3-neck flask equipped with a condenser, a nitrogen in/out let, a mechanical stirrer, a thermo-watch, and a heating mantle, a mixture of 30 g of 35,000 Mw PEG and toluene (80 mL) was heated to 60° C. At this temperature, KOH (0.77 g, 0.02 mol, in 1 g of water) was added and the reaction mixture was stirred for 1 hour. 2-Ethyl hexyl glycidyl ether (1.91 g, 0.02 mole) was added and the reaction temperature was kept at 110° C. for 5 hours. After the reaction mass was cooled to 60° C., toluene (80 mL) was further added. The solution was precipitated into 300 mL of hexane. After filtration and washing with ethyl acetate (100 mL×3×) and drying in vacuum, a white polymer (31 g) was obtained. 1H NMR showed 5.2% hydrophobe incorporation. The Brookfield viscosity of a 5% aqueous solution of this oligomer was >200,000 cps (BF LV, S-63, 0.3 rpm at 25° C.). Paint performance: SG10 M (standard formulation). TE %=0.11, Viscosity Loss upon Tinting (VLT)=−24 KU. For UCAR 379 G, TE %=0.28, VLT=−30 KU. In a 250 mL, round bottom 3-neck flask equipped with a condenser the reaction temperature was kept at 110° C. for 5 hours After the reaction mass was cooled to 60° C. The solution was precipitated into 300 mL of hexane After filtration washing with ethyl acetate (100 mL×3×) drying in vacuum

Conditions: temp:78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a four-necked 200-mL flask equipped with a reflux cooling tube, a dropping funnel, a thermometer and a stirring blade, 9.4 g (53.7 mmol) of L(+)-arginine, 50.0 g of water and 50.0 g of ethanol were placed, and the mixture was heated to 78° C. while being stirred under a nitrogen atmosphere. Subsequently, the inside of the reaction system was maintained at 78 to 80° C., 10.0 g (53.7 mmol) of 2-ethylhexyl glycidyl ether was added dropwise thereto. Thereafter, the mixture was aged for 4 hours at 78 to 80° C., and then was returned to room temperature. Subsequently, 9.8 g (53.7 mmol) of a 6 mol/L aqueous solution of hydrochloric acid was added thereto to neutralize the mixture. Water and ethanol were completely distilled off from the reaction solution under reduced pressure, and thus 21.6 g of N-[2-hydroxy-3-(2-ethylhexyl)oxypropyl]-L-arginine hydrochloride was obtained as a white solid. This compound corresponds to the compound 2 of Table 1. In a four-necked 200-mL flask equipped with a reflux cooling tube, a dropping funnel Subsequently, the inside of the reaction system was maintained at 78 to 80° C. was returned to room temperature Water and ethanol were completely distilled off from the reaction solution under reduced pressure

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

Procedure: If the butyl glycidyl ether is replaced by 2-ethylhexyl glycidyl ether, 2,4-di{2-hydroxy-4-[3-(2-ethylhexoxy)-2-hydroxypropoxy]phenyl}-6-methoxy-1,3,5-triazine having a melting point of 98°-99° C. is obtained. is obtained

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.9 g (0.10 mole) of ethyl carbamate was dissolved in 18.6 g (0.10 mole) of 2-ethylhexyl glycidyl ether. After adding 0.41 g of N, N-dimethylbenzylamine and 0 63 g of di-n-butyltin dilaurate, the solution was heated at 160° C. for 1 hour while blowing nitrogen gas into the reaction mixture. The product was distilled under reduced pressure to give 20.0 g (88% of theory) of 5-(2-ethylhexyl) oxymethyl-2-oxazolidinone. The product was distilled under reduced pressure

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

Procedure: 5 g of solid sodium hydrogen sulfide monohydrate are saturated with hydrogen sulfide at room temperature in 250 ml of methanol. Then 186 g (1 mole) of 2-ethylhexyl glycidyl ether are added dropwise at room temperature and with efficient stirring in the course of 2 hours, while simultaneously introducing hydrogen sulfide gas. The flow of hydrogen sulfide gas is constantly introduced in an amount just sufficient for the reaction solution to take up. The temperature should not exceed 30°-40° C. in order effectively to prevent the formation of corresponding thioethers. When the reaction of the epoxide is complete, the catalyst is destroyed with a small amount of dilute sulfuric acid and the reaction mixture is extracted with ether. The ethereal extract is washed neutral with water, dried over magnesium sulfate and the solvent is removed. Distillation of the residue at 75° C./10-3 torr yields the pure monothioglycerol 2-ethylhexyl ether with a SH content of 14.8%. exceed 30°-40° C. in order the catalyst is destroyed with a small amount of dilute sulfuric acid the reaction mixture is extracted with ether The ethereal extract is washed neutral with water dried over magnesium sulfate the solvent is removed Distillation of the residue at 75° C./10-3 torr

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

Procedure: 5 g of solid sodium hydrogen sulfide monohydrate are saturated with hydrogen sulfide at room temperature in 250 ml of methanol. Then 186 g (1 mole) of 2-ethylhexyl glycidyl ether are added dropwise at room temperature and with efficient stirring in the course of 2 hours, while simultaneously introducing hydrogen sulfide gas. The flow of hydrogen sulfide gas is constantly introduced in an amount just sufficient for the reaction solution to take up. The temperature should not exceed 30°-40° C. in order effectively to prevent the formation of corresponding thioethers. When the reaction of the epoxide is complete, the catalyst is destroyed with a small amount of dilute sulfuric acid and the reaction mixture is extracted with ether. The ethereal extract is washed neutral with water, dried over magnesium sulfate and the solvent is removed. Distillation of the residue at 75° C./10-3 torr yields the pure monothioglycerol 2-ethylhexyl ether with a SH content of 14.8%. exceed 30°-40° C. in order the catalyst is destroyed with a small amount of dilute sulfuric acid the reaction mixture is extracted with ether The ethereal extract is washed neutral with water dried over magnesium sulfate the solvent is removed Distillation of the residue at 75° C./10-3 torr

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

Procedure: 4-(1,1-dioxo-thiomorpholin-4-yl)phenol (4.1 g, 18 mmol), 2-ethylhexyl glycidyl ether (4.4 g, 23,6 mmol) and ethyltriphenylphosphonium bromide (0.37 g) are heated under nitrogen for 5 h at 145° C. and the crude product is chromatographed over silica gel (hexane/ethylacetate 1:1) to afford a colourless liquid 5.2 g (70%). the crude product is chromatographed over silica gel (hexane/ethylacetate 1:1)

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

Procedure: 4-(1,1-dioxo-thiomorpholin-4-yl)phenol (4.1 g, 18 mmol), 2-ethylhexyl glycidyl ether (4.4 g, 23,6 mmol) and ethyltriphenylphosphonium bromide (0.37 g) are heated under nitrogen for 5 h at 145° C. and the crude product is chromatographed over silica gel (hexane/ethylacetate 1:1) to afford a colourless liquid 5.2 g (70%). the crude product is chromatographed over silica gel (hexane/ethylacetate 1:1)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a flame dried, 500 mL round bottomed flask equipped with an addition funnel charged with epichlorohydrin (15.62 g, 0.17 moles), is added 2-ethylhexanol (16.5 g, 0.127 moles) and stannic chloride (0.20 g, 0.001 moles). The reaction is kept under an argon atmosphere and warmed to 90° C. using an oil bath. Epichlorohydrin is dripped into the stirring solution over 60 minutes followed by stirring at 90° C. for 18 hours. The reaction is fitted with a vacuum distillation head and 1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol is distilled under 0.2 mm Hg. The 1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol (4.46 g, 0.020 moles) is dissolved in tetrahydrofuran (50 mL) and stirred at room temperature under an argon atmosphere. To the stirring solution is added potassium tert-butoxide (2.52 g, 0.022 moles) and the suspension is stirred at room temperature for 18 hours. The reaction is then evaporated to dryness, residue dissolved in hexanes and washed with water (100 mL). The hexanes phase is separated, dried with Na2SO4, filtered and evaporated to dryness to yield the crude 2-ethylhexyl glycidyl ether, which can be further purified by vacuum distillation. To a flame dried 500 mL round bottomed flask equipped with an addition funnel is distilled under 0.2 mm Hg stirred at room temperature under an argon atmosphere the suspension is stirred at room temperature for 18 hours The reaction is then evaporated to dryness, residue dissolved in hexanes washed with water (100 mL) The hexanes phase is separated dried with Na2SO4 filtered evaporated to dryness

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a flame dried, 500 mL round bottomed flask equipped with an addition funnel charged with epichlorohydrin (15.62 g, 0.17 moles), is added 2-ethylhexanol (16.5 g, 0.127 moles) and stannic chloride (0.20 g, 0.001 moles). The reaction is kept under an argon atmosphere and warmed to 90° C. using an oil bath. Epichlorohydrin is dripped into the stirring solution over 60 minutes followed by stirring at 90° C. for 18 hours. The reaction is fitted with a vacuum distillation head and 1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol is distilled under 0.2 mm Hg. The 1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol (4.46 g, 0.020 moles) is dissolved in tetrahydrofuran (50 mL) and stirred at room temperature under an argon atmosphere. To the stirring solution is added potassium tert-butoxide (2.52 g, 0.022 moles) and the suspension is stirred at room temperature for 18 hours. The reaction is then evaporated to dryness, residue dissolved in hexanes and washed with water (100 mL). The hexanes phase is separated, dried with Na2SO4, filtered and evaporated to dryness to yield the crude 2-ethylhexyl glycidyl ether, which can be further purified by vacuum distillation. To a flame dried 500 mL round bottomed flask equipped with an addition funnel is distilled under 0.2 mm Hg stirred at room temperature under an argon atmosphere the suspension is stirred at room temperature for 18 hours The reaction is then evaporated to dryness, residue dissolved in hexanes washed with water (100 mL) The hexanes phase is separated dried with Na2SO4 filtered evaporated to dryness

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

Procedure: 4-(1,1-dioxo-thiomorpholin-4-yl)phenol (4.1 g, 18 mmol), 2-ethylhexyl glycidyl ether (4.4 g, 23,6 mmol) and ethyltriphenylphosphonium bromide (0.37 g) are heated under nitrogen for 5 h at 145° C. and the crude product is chromatographed over silica gel (hexane/ethylacetate 1:1) to afford a colourless liquid 5.2 g (70%). the crude product is chromatographed over silica gel (hexane/ethylacetate 1:1)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a flame dried, 500 mL round bottomed flask equipped with an addition funnel charged with epichlorohydrin (15.62 g, 0.17 moles), is added 2-ethylhexanol (16.5 g, 0.127 moles) and stannic chloride (0.20 g, 0.001 moles). The reaction is kept under an argon atmosphere and warmed to 90° C. using an oil bath. Epichlorohydrin is dripped into the stirring solution over 60 minutes followed by stirring at 90° C. for 18 hours. The reaction is fitted with a vacuum distillation head and 1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol is distilled under 0.2 mm Hg. The 1-chloro-3-(2-ethyl-hexyloxy)-propan-2-ol (4.46 g, 0.020 moles) is dissolved in tetrahydrofuran (50 mL) and stirred at room temperature under an argon atmosphere. To the stirring solution is added potassium tert-butoxide (2.52 g, 0.022 moles) and the suspension is stirred at room temperature for 18 hours. The reaction is then evaporated to dryness, residue dissolved in hexanes and washed with water (100 mL). The hexanes phase is separated, dried with Na2SO4, filtered and evaporated to dryness to yield the crude 2-ethylhexyl glycidyl ether, which can be further purified by vacuum distillation. To a flame dried 500 mL round bottomed flask equipped with an addition funnel is distilled under 0.2 mm Hg stirred at room temperature under an argon atmosphere the suspension is stirred at room temperature for 18 hours The reaction is then evaporated to dryness, residue dissolved in hexanes washed with water (100 mL) The hexanes phase is separated dried with Na2SO4 filtered evaporated to dryness