pentanoic 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:

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:

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: In reaction 19, cyclohexane was oxidized to a 1:7.1:6.0 mixture of adipic acid, cyclohexanone and cyclohexanol after 5 hours (turnovers: 21 (acid), 149 (ketone), 126 (alcohol); ˜6 % total conversion). The crude adipic acid product was collected by filtration after cooling the reaction mixture. Analyses of the isolated adipic acid were performed using elemental analysis, mass spectrometry, infrared spectroscopy, and 1H/13C NMR with comparisons to an authentic adipic acid sample. All analytical results showed that the isolated adipic acid (crude, washed with o-dichlorobenzene, but not recrystallized) was >95 % pure. NMR analysis showed that glutaric acid was also produced (<5 %) along with much lower amounts of shorter chain acids such as formic acid, butyric acid, valeric acid, etc. Only trace amounts of ketone and alcohol (and no adipic acid) were observed when the catalyst is omitted or replaced with 3 equivalents of dpphen alone. The crude adipic acid product was collected by filtration after cooling the reaction mixture All analytical results washed with o-dichlorobenzene not recrystallized)

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

Procedure: A mixture of methyl 5-[(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy]pentanoate (14 g., 0.0339 mole), acetic acid (100 ml) and 6N hydrochloric acid (50 ml) is stirred and refluxed for 6 hours. The mixture is poured into water (400 ml) and the product which solidifies upon standing is removed by filtration and dried. The product is recrystallized from a mixture of tetrahydrofuran, ether and petroleum ether (50/100/200 ml) to give 12.5 g, of 5-[6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1-inden-5-yl)oxy)pentanoic acid, m.p. 106°-108° C. refluxed for 6 hours upon standing is removed by filtration dried The product is recrystallized from a mixture of tetrahydrofuran, ether and petroleum ether (50/100/200 ml) to give 12.5 g

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

Procedure: A mixture of methyl 5-[(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy]pentanoate (14 g., 0.0339 mole), acetic acid (100 ml) and 6N hydrochloric acid (50 ml) is stirred and refluxed for 6 hours. The mixture is poured into water (400 ml) and the product which solidifies upon standing is removed by filtration and dried. The product is recrystallized from a mixture of tetrahydrofuran, ether and petroleum ether (50/100/200 ml) to give 12.5 g, of 5-[(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy)]pentanoic acid, m.p. 106°-108° C. refluxed for 6 hours upon standing is removed by filtration dried The product is recrystallized from a mixture of tetrahydrofuran, ether and petroleum ether (50/100/200 ml) to give 12.5 g