7-methoxy-3,7-dimethyloctan-1-ol

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

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

Procedure: The mesylate of each of 7-methoxy-3,7-dimethyloctan-1-ol, 7-methoxy-3,7-dimethyloct-2-en-1-ol and 6-methoxy-6-methylheptan-2-ol is reacted with p-ethylphenol using the process of Example 10(D) to yield 7-methoxy-3,7-dimethyloctyl p-ethylphenyl ether, 7-methoxy-3,7-dimethyloct-2-enyl p-ethylphenyl ether and 6-methoxy-6-methylhept-2-yl p-phenyl ether (5-methoxy-1,5-dimethylhexyl p-ethylphenyl ether).

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

Procedure: 3.76 g. of 3,7-dimethyl-7-methoxy-1-octanol are dissolved in 20 ml. of anhydrous pyridine and mixed, while stirring and with ice cooling, with 4.2 g. of p-toluenesulfochloride. Subsequently, the solution is left overnight at 5° C., then poured onto ice-water and extracted three times with diethyl ether. The extracts are washed successively with cold 2-N aqueous hydrochloric acid solution, water and twice with saturated aqueous sodium chloride solution, dried over sodium sulfate/potassium carbonate and evaporated under reduced pressure, finally at 0.05 mmHg. There is obtained 3,7-dimethyl-7-methoxy-octyl p-toluenesulfonate; nD20 = 1.4927. poured onto ice-water extracted three times with diethyl ether The extracts are washed successively with cold 2-N aqueous hydrochloric acid solution, water and twice with saturated aqueous sodium chloride solution dried over sodium sulfate/potassium carbonate evaporated under reduced pressure, finally at 0.05 mmHg

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

Procedure: 93.2 g. of 7-methoxycitronellal dissolved in 200 ml. of absolute diethyl ether are added dropwise with ice cooling to a suspension of 7.6 g. of lithium aluminum hydride in 500 ml. of absolute diethyl ether. Subsequently, the mixture is stirred for 30 minutes and decomposed in the cold by the addition of 100 ml. of aqueous ammonium chloride solution. The resulting mass is filtered through diatomaceous earth, the filtrate washed once with saturated aqueous ammonium chloride solution and once with saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. The residue is distilled at 0.1 mmHg. There is obtained pure 3,7-dimethyl-7-methoxy-1-octanol of boiling point 87° C./0.1 mmHg; nD20 = 1.4456. decomposed in the cold by the addition of 100 ml The resulting mass is filtered through diatomaceous earth the filtrate washed once with saturated aqueous ammonium chloride solution and once with saturated aqueous sodium chloride solution dried over sodium sulfate evaporated The residue is distilled at 0.1 mmHg

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

Procedure: A mixture consisting of 5.4 g (0.025 mol) of p-nitrobenzyl bromide and 4.15 g (0.025 mol) of triethyl phosphite is stirred at 90°, over the course of 1 hour and under nitrogen. The resulting ethyl bromide is distilled off from the reaction vessel. The obtained solution is then evacuated and stirred at a bath temperature of 110° for one further hour in a water jet vacuum. A suspension consisting of 1.68 g (0.030 mol) of sodium methylate and 10 cc of absolute dimethylformamide is carefully added at 0° to the residue. 4.65 g (0.025 mol) of 7-methoxy-3,7-dimethyloctanol in a small amount of dimethylformamide are subsequently added over the course of 5 minutes to the red reaction mixture which is stirred at 0° for 1 hour and at room temperature for 90 minutes. The ruby-coloured solution gradually turns dark brown. 60 cc of water are added and the reaction mixture is extracted with hexane. The extracts are washed with water and saturated sodium chloride solution, dried over magnesium sulphate and evaporated at 40° /20 mm Hg. After chromatography of the residue on silica gel with hexane/ethyl acetate (97:3) and (94:6), pure 1-(8-methoxy-4,8-dimethyl-1-nonenyl)-4-nitrobenzene is obtained as a slightly yellow oil. nD20 = 1.5473 The resulting ethyl bromide is distilled off from the reaction vessel The obtained solution is then evacuated stirred at a bath temperature of 110° for one further hour in a water jet vacuum is carefully added at 0° to the residue is stirred at 0° for 1 hour and at room temperature for 90 minutes the reaction mixture is extracted with hexane The extracts are washed with water and saturated sodium chloride solution dried over magnesium sulphate evaporated at 40° /20 mm Hg