3,5,5-trimethylhexanal

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-Ethyl-5,7,7-trimethyloctanal was prepared from 3,5,5-trimethylhexanal and n-butanal similarly to Examples 1 and 2; it was obtained in the form of a diastereomeric mixture. it was obtained in the form of a diastereomeric mixture

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

Procedure: 2-Ethyl-5,7,7-trimethyloctanal was prepared from 3,5,5-trimethylhexanal and n-butanal similarly to Examples 1 and 2; it was obtained in the form of a diastereomeric mixture. it was obtained in the form of a diastereomeric mixture

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

Procedure: 128 g (4 moles) of methanol and 2 g (0.05 mole) of NaOH were initially taken under nitrogen in a reaction flask and were refluxed. A mixture of 142 g (1 mole) of 3,5,5-trimethylhexanal and 116 g (2 moles) of propionaldehyde was added dropwise to this solution in the course of 10 minutes. The resulting reaction mixture was kept at the boil for 1 hour (h) and then brought to pH 4-5 with an 80% strength aqueous acetic acid solution. After washing twice with water, the organic phase was separated off and worked up by fractional distillation. 32 g of unconverted 3,5,5-trimethylhexanal, as light ends, and 113 g of 2,5,7,7-tetramethyl-2-octenal (bp.=108°-111° C./14 mbar) were obtained, corresponding to a selectivity of 81%, based on trimethylhexanal; nD25 =1.4580. were refluxed was added dropwise to this solution in the course of 10 minutes The resulting reaction mixture After washing twice with water the organic phase was separated off worked up by fractional distillation

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

Procedure: 128 g (4 moles) of methanol and 2 g (0.05 mole) of NaOH were initially taken under nitrogen in a reaction flask and were refluxed. A mixture of 142 g (1 mole) of 3,5,5-trimethylhexanal and 116 g (2 moles) of propionaldehyde was added dropwise to this solution in the course of 10 minutes. The resulting reaction mixture was kept at the boil for 1 hour (h) and then brought to pH 4-5 with an 80% strength aqueous acetic acid solution. After washing twice with water, the organic phase was separated off and worked up by fractional distillation. 32 g of unconverted 3,5,5-trimethylhexanal, as light ends, and 113 g of 2,5,7,7-tetramethyl-2-octenal (bp.=108°-111° C./14 mbar) were obtained, corresponding to a selectivity of 81%, based on trimethylhexanal; nD25 =1.4580. were refluxed was added dropwise to this solution in the course of 10 minutes The resulting reaction mixture After washing twice with water the organic phase was separated off worked up by fractional distillation

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Starting from (1-(2-naphthyl)ethyltriphenylphosphonium bromide (2.80 g, 5.63 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 3.5 mL, 5.63 mmol, 1.0 equiv.) and 3,5,5-trimethylhexanal (1.20 g, 8.44 mmol, 1.5 equiv.), and after stirring the mixture at 25° C. for 3 h, 0.73 g (46%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3).

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Starting from (1-(2-naphthyl)ethyltriphenylphosphonium bromide (2.80 g, 5.63 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 3.5 mL, 5.63 mmol, 1.0 equiv.) and 3,5,5-trimethylhexanal (1.20 g, 8.44 mmol, 1.5 equiv.), and after stirring the mixture at 25° C. for 3 h, 0.73 g (46%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3).

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

Procedure: Starting from phenethyltriphenylphosphonium bromide (2.80 g, 6.26 mmol, 1.0 equiv.), n-BuLi (1.6 M in hexanes, 3.9 mL, 6.26 mmol, 1.0 equiv.) and 3,5,5-trimethylhexanal (1.33 g, 9.39 mmol, 1.5 equiv.), 0.94 g (65%) of the title compound as a colorless oil was obtained after purification by flash chromatography on SiO2 (cyclohexane/EtOAc 997:3).

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: To a mixture of the 3,5,5-trimethylhexanal (17.4 mL, 0.10 mol), ammonium chloride (53.5 g, 0.205 mol) and diethyl ether (113 mL) was added sodium cyanide (7.35 g, 0.15 mol) in water (38 mL). The reaction mixture was allowed to stir vigorously for 16 h. The layers were separated. The aqueous layer was extracted with diethyl ether. The combined organic layer was then extracted with 1 N HCl. Saturated sodium bicarbonate was then added until 1-cyano-3,5,5-trimethyl-hexylamine was completely precipitated. Vacuum filtration and washing with 5 mL ice cold water followed by lyophilization gave 1-cyano-3,5,5-trimethylhexylamine (5.805 g, 0.034 mol, 34.5%) as a white solid. The layers were separated The aqueous layer was extracted with diethyl ether The combined organic layer was then extracted with 1 N HCl Saturated sodium bicarbonate was then added until 1-cyano-3,5,5-trimethyl-hexylamine was completely precipitated Vacuum filtration washing with 5 mL ice cold water