2-methyl-3-phenylpropan-1-ol

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

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: 2-Methyl-3-phenylpropanol (219 g., 1.46 mol.) and 10.30 g. of 50% Ni on silica catalyst (4.7 wt %, G-49-C, United Catalyst) were stirred at 700 rpm in a Parr reactor at 150° C. and 200-600 psi of hydrogen until hydrogen absorption stopped (12 hours). Utilizing 2 wt. % of the catalyst requires that the reaction be run at 180° C. The reaction mixture was filtered through a filter bed (Celite™) using toluene as a rinse solvent and concentrated to a clear, colorless liquid. The odor grade product was isolated by fractional distillation, 174 g., 80% yield; bp 80° C. at 4 mm. Odor: very pleasant green, fruity, rosy. Mass Spectrum from 5508-36. MS (El) m/z (relative intensity) 138 (M+−H2O, 15), 123 (M+−Me and H2O, 15). 200-600 psi of hydrogen until hydrogen absorption (12 hours) be run at 180° C The reaction mixture was filtered through a filter bed (Celite™) concentrated to a clear, colorless liquid The odor grade product was isolated by fractional distillation, 174 g

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

Procedure: 2-Methyl-3-phenylpropanol (219 g., 1.46 mol.) and 10.30 g. of 50% Ni on silica catalyst (4.7 wt %, G-49-C, United Catalyst) were stirred at 700 rpm in a Parr reactor at 150° C. and 200-600 psi of hydrogen until hydrogen absorption stopped (12 hours). Utilizing 2 wt. % of the catalyst requires that the reaction be run at 180° C. The reaction mixture was filtered through a filter bed (Celite™) using toluene as a rinse solvent and concentrated to a clear, colorless liquid. The odor grade product was isolated by fractional distillation, 174 g., 80% yield; bp 80° C. at 4 mm. Odor: very pleasant green, fruity, rosy. Mass Spectrum from 5508-36. MS (El) m/z (relative intensity) 138 (M+−H2O, 15), 123 (M+−Me and H2O, 15). 200-600 psi of hydrogen until hydrogen absorption (12 hours) be run at 180° C The reaction mixture was filtered through a filter bed (Celite™) concentrated to a clear, colorless liquid The odor grade product was isolated by fractional distillation, 174 g

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: DE 29 52 719 likewise describes the iron chloride-catalyzed Friedel-Crafts alkylation of 2-methyl-3-phenylpropanol. In cyclohexane or dichloroethane solvent, a yield of 84-86% of 2-methyl-3-(4-tert-butylphenyl)propanol was obtained. The formation of the misomeric compound, (2-methyl-3-(3-tert-butylphenyl)propanol), was not demonstrated.

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

Procedure: DE 29 52 719 likewise describes the iron chloride-catalyzed Friedel-Crafts alkylation of 2-methyl-3-phenylpropanol. In cyclohexane or dichloroethane as solvent, a yield of 84-86% of 2-methyl-3-(4-tert-butylphenyl)propanol was obtained. The formation of the m-isomeric compound (2-methyl-3-(3-tert-butylphenyl)propanol), was not demonstrated. A disadvantage of the described Friedel-Crafts alkylations is the small amount of the m-isomeric compound formed (m:p ratio is max. 1:5).

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

Procedure: DE 29 52 719 likewise describes the iron chloride-catalyzed Friedel-Crafts alkylation of 2-methyl-3-phenylpropanol. In cyclohexane or dichloroethane as solvent, a yield of 84-86% of 2-methyl-3-(4-tert-butylphenyl)propanol was obtained. The formation of the m-isomeric compound (2-methyl-3-(3-tert-butylphenyl)propanol), was not demonstrated. A disadvantage of the described Friedel-Crafts alkylations is the small amount of the m-isomeric compound formed (m:p ratio is max. 1:5).

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

Procedure: 220 ml (1.9 mole) of KH (35% in oil) were placed, under a N2 -atmosphere, into a 4.5 l reactor and washed 4 times with pentane, in order to remove all traces of oil. 1.5 l of dry tetrahydrofurane were added before the dropwise addition of a solution of 259 g (1.73 mole) of 1-hydroxy-2-methyl-3-phenylpropane and 500 ml of dry tetrahydrofurane. The reaction was stirred for 15 hours at room temperature. Then 285 g (2.01 mole) of methyl iodide were added dropwise over a period of 2 hours, and stirring was continued at room temperature for another 2 hours. A possible excess of KH was hydrolyzed by adding 50 ml of methanol, then the reaction mixture was poured on ice. The product was taken up in ether, which was washed 3 times with a saturated NH4Cl solution and then with brine to neutrality. After drying over Na2SO4, the solution was filtered, concentrated and then distilled over a Vigreux-type column (boiling point: 100° C. at 5×102Pa). into a 4.5 l reactor and washed 4 times with pentane in order to remove all traces of oil stirring was continued at room temperature for another 2 hours the reaction mixture was poured on ice which was washed 3 times with a saturated NH4Cl solution After drying over Na2SO4 the solution was filtered concentrated distilled over a Vigreux-type column (boiling point: 100° C. at 5×102Pa)

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

Procedure: α-methylcinnamaldehyde was hydrogenated using copper chromite (2% by weight) as catalyst at a temperature of 150° C. and a pressure of 130° C. psig hydrogen. After the uptake of hydrogen ceased, the mixture was filtered and distilled to obtain the 2-methyl-3-phenylpropanol (b.pt 100° C./1 mm). at a temperature of 150° C. the mixture was filtered distilled