3,7-dimethyloctanoic acid

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: 3,7-dimethyloctanoic acid was dissolved in thionyl chloride (10 ml) and treated in water bath for 3 hours to distill off excess thionyl chloride. Ethanol (30 ml) was added to chloride of 3,7-dimethyloctanoic acid and refluxed in water bath for 2 hours. After cooling, the reaction mixture was added to 1N HCl (80 ml) to be acidic and distributed with EtOAc. The distributed liquid was purified with column chromatography (developing solvent: C6H14-EtOAc (3:1)) after concentration, and the 3,7-dimethyloctanoic acid ethyl ester shown in the following was isolated. 3,7-dimethyloctanoic acid was obtained by contact reduction of geranic acid. to distill off excess thionyl chloride Ethanol (30 ml) was added to chloride of 3,7-dimethyloctanoic acid refluxed in water bath for 2 hours After cooling the reaction mixture was added to 1N HCl (80 ml) The distributed liquid was purified with column chromatography (developing solvent: C6H14-EtOAc (3:1)) after concentration following was isolated

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

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

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of chromium trioxide (55.5 g, 0.555 mol) in water (68 ml) and 2M-sulphuric acid (12 ml) was added dropwise to a solution of 3,7-dimethyloctanol (43.7 g, 0.308 mol) in acetone (100 ml), the temperature was maintained at 40-60° C. and the reaction mixture was left stirring overnight. Acetone was carefully removed in vacuo, the reaction mixture was diluted in water and washed with diethyl ether (2×200 ml). The ethereal solution was washed with 10% sodium hydroxyde solution (200 ml); and the aqueous phase was acidified with 36% HCl (200 ml) and washed once more with diethyl ether (2×200 ml). The organic layer was dried (MgSO4) and the diethyl ether was removed in vacuo. The crude product was distilled to give a colourless oil. the reaction mixture was left Acetone was carefully removed in vacuo the reaction mixture was diluted in water washed with diethyl ether (2×200 ml) The ethereal solution was washed with 10% sodium hydroxyde solution (200 ml) washed once more with diethyl ether (2×200 ml) The organic layer was dried (MgSO4) the diethyl ether was removed in vacuo The crude product was distilled to give a colourless oil

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

Procedure: 3,7-dimethyloctanoic acid was dissolved in thionyl chloride (10 ml) and treated in water bath for 3 hours to distill off excess thionyl chloride. Ethanol (30 ml) was added to chloride of 3,7-dimethyloctanoic acid and refluxed in water bath for 2 hours. After cooling, the reaction mixture was added to 1N HCl (80 ml) to be acidic and distributed with EtOAc. The distributed liquid was purified with column chromatography (developing solvent: C6H14-EtOAc (3:1)) after concentration, and the 3,7-dimethyloctanoic acid ethyl ester shown in the following was isolated. 3,7-dimethyloctanoic acid was obtained by contact reduction of geranic acid. to distill off excess thionyl chloride Ethanol (30 ml) was added to chloride of 3,7-dimethyloctanoic acid refluxed in water bath for 2 hours After cooling the reaction mixture was added to 1N HCl (80 ml) The distributed liquid was purified with column chromatography (developing solvent: C6H14-EtOAc (3:1)) after concentration following was isolated