2-methylpentan-1-ol

Conditions: temp:145.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Magnesium powder 6.65 gm, (0.273 moles) along with 225.0 ml Isopar "H" hydrocarbon solvent and 0.20 gm of iodine crystals were placed in a 3-necked reaction flask under an argon atmosphere. This mixture was heated under the argon atmosphere to 145° C. for about 60 minutes for metal activation. n-Butyl chloride (40 ml, 0.385 moles) was then gradually added to the reaction slurry in 30 minutes. The heating was cut off due to exothermic reaction and reflux. The reaction of the slurry was continued for about two hours at reflux temperature. The reflux temperature during this period dropped to about 110° C. The reflux solvent contained alkenes (i.e., butene/octene, etc.). After two hours of reaction, heating was cut off and then, the first 15 ml of 2-methyl-1-pentanol of a total of 60 ml was added drop by drop to the reaction slurry. On addition of this alcohol, butane was released with exothermic reaction and the slurry turned into a thick gum-like gel. When the temperature dropped to about 50° C., the remaining 45 ml of 2-methyl-1-pentanol, along with 50 ml of Isopar H solvent, was added quickly under good agitation to reduce the viscosity of the slurry. The 2-methyl-1-pentanol reacted with BuMgCl as was evidenced by the release of butane. The reaction fluid containing some grayish particles was heated slowly with reflux. The reflux butane with some alkene, such as butene/octene, was distilled off through the reflux condenser to increase the reaction temperature close to 145° C. It is important to keep the temperature two to three degrees lower than 2-methyl-1-pentanol's reflux temperature (148° C.-150° C.). The reaction was continued at 145° C. for about 30 minutes. The reaction slurry was filtered while hot (90° C.-120° C.). The filtration was fast and completed in about ten minutes. Final volume of the filtrate was about 340 ml. Fine gray suspended particles of solid were collected on the filter. The clear filtrate was analyzed and found to have a 0.79 molar magnesium concentration with about 98% magnesium recovery. The detailed analysis of the liquid product was found to be 0.79 moles magnesium, 0.50 moles 2MPO (as total base), 1.08 moles chloride per liter, along with solvent Isopar H and excess 2-methyl-1-pentanol. The product formula can be presented as The heating was cut off due to exothermic reaction reflux The reaction of the slurry at reflux temperature The reflux temperature during this period dropped to about 110° C After two hours of reaction heating was released with exothermic reaction When the temperature dropped to about 50° C. The reaction fluid containing some grayish particles was heated slowly with reflux The reflux butane with some alkene, such as butene/octene, was distilled off through the reflux condenser to increase the reaction temperature close to 145° C the temperature two to three degrees reflux temperature (148° C.-150° C.) The reaction was continued at 145° C. for about 30 minutes The reaction slurry was filtered while hot (90° C.-120° C.) The filtration completed in about ten minutes were collected on the filter a 0.79 molar magnesium concentration with about 98% magnesium recovery

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure of Example 1, 24.31 gm of magnesium metal powder (1.0 mole) was placed in a 3-necked 3 liter reactor flask, along with 1600 ml of isoparaffinic solvent (Isopar E) having a boiling range of 116°-139° C. and 0.25 gm of iodine crystals. This mixture was heated under an argon atmosphere to reflux temperature for about 60 minutes for metal activation. 105 ml of n-butyl chloride (1.OM) was then gradually added to the reaction slurry in 40 minutes, then reaction was continued for two hours at reflux temperature. Addition of 180 ml (1.4 moles) of 2-methyl-1-pentanol to the reaction slurry was started. The reaction slurry became thick and viscous at reflux temperatures when 60 ml of the 180 ml of the 2-methyl-1-pentanol was added. At this point the reaction slurry was cooled down to 65° C. At 65° C. the remaining 120 ml of 2-methyl-1 -pentanol was added along with 400 ml of solvent (Isopar E) with good agitation to reduce the viscosity of the slurry. The 2-methyl-1-pentanol reacted with BuMgCl as was evidenced by the release of butane. Butane was distilled off through reflux condensor to maintain the reaction temperature close to the reflux temperature of solvent Isopar E. The reaction was continued for two hours. The slurry was filtered while hot, 90°-100° C. The filtration rate was fast and complete in about 10-15 minutes. Final volume of filtrate was about 2100 ml. Fine gray suspended particles as solid were collected on the filter. The clear filtrate was analyzed and found to have 0.435 molar magnesium concentration with 91.40+% magnesium recovery. This filtrate was found to be stable at 0° to 40° C. on storage. was placed in a 3-necked 3 liter reactor flask, along with 1600 ml of isoparaffinic solvent (Isopar E) This mixture was heated under an argon atmosphere to reflux temperature for about 60 minutes for metal activation reaction at reflux temperature was added Butane was distilled off through reflux condensor to maintain the reaction temperature close to the reflux temperature of solvent Isopar E The reaction was continued for two hours The slurry was filtered while hot, 90°-100° C complete in about 10-15 minutes were collected on the filter 0.435 molar magnesium concentration with 91.40+% magnesium recovery to be stable at 0° to 40° C. on storage

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

Procedure: Following the procedure of Example 1, 24.3 gm of magnesium metal chips were placed in a 3 necked 3 liter reactor with 0.25 g I2 crystals and 1500 ml of Isopar G solvent. A fraction of isoparaffinic hydrocarbons (Isopar G) having a boiling range of 157° to 176° C. The magnesium was iodine-activated by heating under argon and at reflux for 90 minutes. The activated magnesium metal slurry in Isopar G was then reacted with 104 ml of n-butyl chloride (lM) at the solvent reflux temperature. After two hours of reaction, 125 ml of 2-methyl-1-pentanol was added slowly with good agitation. The thick reaction slurry was agitated at reflux for two hours. Because of the viscous nature of the thick slurry, it was difficult to filter when it was hot. Therefore, the solvent was removed under reduced pressure at 90°-100° C. The dried solid obtained was not a powder, but sticky gray flakes. Dried product was analyzed and found to contain 15.21% Mg; 58.95% by heating under argon at reflux for 90 minutes reflux temperature was added slowly with good agitation at reflux for two hours to filter when it Therefore, the solvent was removed under reduced pressure at 90°-100° C The dried solid obtained

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

Procedure: To 10 ml of 1.085M DBM in heptane and 0.33 ml of 0.92M TIBAL (as above) is slowly added a mixture of 2-methyl-1-pentanol (0.9 ml, 7.25 mmoles) and isopropanol (1.1 ml, 14.45 mmoles), diluted to 5 ml with cyclohexane. A slurry is formed which dissolves on addition of 0.9 ml (7.25 mmoles) of 2-methyl-1-pentanol. A slurry is formed which

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

Procedure: To 10 ml of 1.085M DBM in heptane and 0.33 ml of 0.92M TIBAL (as above) is slowly added a mixture of 2-methyl-1-pentanol (1.34 ml, 10.85 mmoles) and isopropanol (0.82 ml, 10.85 mmoles) diluted to 5 ml with cyclohexane. Again, a clear, stable solution results at room temperature. Again, a clear, stable solution results at room temperature

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

Procedure: To 10 ml of 1.085M DBM in heptane containing 0.33 ml of 0.92M TIBAL is added slowly a mixture of 2-methyl-1-pentanol (1.80 ml, 14.45 mmoles) and isopropanol (0.55 ml, 7.25 mmoles) diluted to 5 ml with cyclohexane. The solution remains clear throughout the addition (no precipitate formation) and is crystal-clear and somewhat viscous at room temperature. The solution remains clear throughout the addition (no precipitate formation) and is crystal-clear and somewhat viscous at room temperature

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

Procedure: To 10 ml of 1.085M DBM in heptane containing 0.33 ml of 0.92M TIBAL is added slowly a mixture of 2-methyl-1-pentanol (1.80 ml, 14.45 mmoles) and isopropanol (0.55 ml, 7.25 mmoles) diluted to 5 ml with cyclohexane. The solution remains clear throughout the addition (no precipitate formation) and is crystal-clear and somewhat viscous at room temperature. The solution remains clear throughout the addition (no precipitate formation) and is crystal-clear and somewhat viscous at room temperature

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

Procedure: To 10 ml of a solution of 4.33 ml of 2-methyl-1-pentanol in heptane there is added 0.4 ml of 1.91 Molar n-butyllithium in cyclohexane. To the cloudy mixture, there is added, slowly and with good mixing, 15 ml of a 1.036 Molar solution of n-butyl-sec-butylmagnesium in heptane. A clear, colorless, viscous solution of magnesium 2-methyl-1-pentyloxide is obtained. To the cloudy mixture, there is added

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

Procedure: To a volume of 10 ml of 1.156 Molar n-butyl-sec-butyl-magnesium (11.56 mmoles) there is added 1.43 ml (11.56 mmoles) of 2-methyl-1-pentanol, diluted to 5 ml with heptane. Then, 0.6 ml of 0.99 Molar (0.59 mmoles) of potassium tert-amylate in cyclohexane solution is added, followed by an additional 1.43 ml of 2-methyl-1-pentanol (11.56 mmoles). A pale yellow, clear, slightly viscous solution of magnesium 2-methyl-1-pentyloxide is obtained. No excess of 2-methyl-1-pentanol is added as in comparative Example I(a).

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

Procedure: To a volume of 10 ml of 1.156 Molar n-butyl-sec-butyl-magnesium (11.56 mmoles) there is added 1.43 ml (11.56 mmoles) of 2-methyl-1-pentanol, diluted to 5 ml with heptane. Then, 0.6 ml of 0.99 Molar (0.59 mmoles) of potassium tert-amylate in cyclohexane solution is added, followed by an additional 1.43 ml of 2-methyl-1-pentanol (11.56 mmoles). A pale yellow, clear, slightly viscous solution of magnesium 2-methyl-1-pentyloxide is obtained. No excess of 2-methyl-1-pentanol is added as in comparative Example I(a).

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in a manner similar to 2-methylhexan-2-yl acetate, except using 2-methylpentan-2-ol. A 500 mL round bottom flask was charged with pyridine (30 mL), 2-methylpentanol (30 mL, 208 mmol) and was added followed by DMAP (1.213 g, 9.93 mmol). Acetic anhydride (46 mL, 417 mmol) was added slowly and the mixture heated at 70° C. for 20 hours. The reaction was quenched by pouring into a 10° C. Et2O bath on ice. 200 mL of water was added and the mixture was extracted with saturated CuSO4 (4×50 mL). The mixture was then washed with water (2×200 mL), saturated NaHCO3 (1×50 mL) and brine (1×50 mL). Mixture was dried with sodium sulfate, filtered and concentrated in vacuo. Distillation of the concentrate at 90° C. at reduced pressure (100 mtorr) resulted in 95% pure 2-methylpentan-2-yl acetate. 1H-NMR: 400 MHz, (CDCl3): 1.91 (s, 3H); 1.69-1.5 (m, 2H); 1.37 (s, 6H); 1.31-1.25 (m, 2H); 0.87 (t J=7.2 Hz, 3H). was added The reaction was quenched by pouring into a 10° C 200 mL of water was added the mixture was extracted with saturated CuSO4 (4×50 mL) The mixture was then washed with water (2×200 mL), saturated NaHCO3 (1×50 mL) and brine (1×50 mL) Mixture was dried with sodium sulfate filtered concentrated in vacuo Distillation of the concentrate at 90° C. at reduced pressure (100 mtorr) resulted in 95% pure 2-methylpentan-2-yl acetate

Conditions: temp:145.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Magnesium powder 6.65 gm, (0.273 moles) along with 225.0 ml Isopar "H" hydrocarbon solvent and 0.20 gm of iodine crystals were placed in a 3-necked reaction flask under an argon atmosphere. This mixture was heated under the argon atmosphere to 145° C. for about 60 minutes for metal activation. n-Butyl chloride (40 ml, 0.385 moles) was then gradually added to the reaction slurry in 30 minutes. The heating was cut off due to exothermic reaction and reflux. The reaction of the slurry was continued for about two hours at reflux temperature. The reflux temperature during this period dropped to about 110° C. The reflux solvent contained alkenes (i.e., butene/octene, etc.). After two hours of reaction, heating was cut off and then, the first 15 ml of 2-methyl-1-pentanol of a total of 60 ml was added drop by drop to the reaction slurry. On addition of this alcohol, butane was released with exothermic reaction and the slurry turned into a thick gum-like gel. When the temperature dropped to about 50° C., the remaining 45 ml of 2-methyl-1-pentanol, along with 50 ml of Isopar H solvent, was added quickly under good agitation to reduce the viscosity of the slurry. The 2-methyl-1-pentanol reacted with BuMgCl as was evidenced by the release of butane. The reaction fluid containing some grayish particles was heated slowly with reflux. The reflux butane with some alkene, such as butene/octene, was distilled off through the reflux condenser to increase the reaction temperature close to 145° C. It is important to keep the temperature two to three degrees lower than 2-methyl-1-pentanol's reflux temperature (148° C.-150° C.). The reaction was continued at 145° C. for about 30 minutes. The reaction slurry was filtered while hot (90° C.-120° C.). The filtration was fast and completed in about ten minutes. Final volume of the filtrate was about 340 ml. Fine gray suspended particles of solid were collected on the filter. The clear filtrate was analyzed and found to have a 0.79 molar magnesium concentration with about 98% magnesium recovery. The detailed analysis of the liquid product was found to be 0.79 moles magnesium, 0.50 moles 2MPO (as total base), 1.08 moles chloride per liter, along with solvent Isopar H and excess 2-methyl-1-pentanol. The product formula can be presented as The heating was cut off due to exothermic reaction reflux The reaction of the slurry at reflux temperature The reflux temperature during this period dropped to about 110° C After two hours of reaction heating was released with exothermic reaction When the temperature dropped to about 50° C. The reaction fluid containing some grayish particles was heated slowly with reflux The reflux butane with some alkene, such as butene/octene, was distilled off through the reflux condenser to increase the reaction temperature close to 145° C the temperature two to three degrees reflux temperature (148° C.-150° C.) The reaction was continued at 145° C. for about 30 minutes The reaction slurry was filtered while hot (90° C.-120° C.) The filtration completed in about ten minutes were collected on the filter a 0.79 molar magnesium concentration with about 98% magnesium recovery