1-bromo-4-propylcyclohexane

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:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 142 g (1.0 mol) of trans-4-propylcyclohexanol was stirred at room temperature and 136 g (0.5 mol) of PBr3 was added drop-wise. The reaction was exothermic and reached about 80° C. The product of the reaction was stirred over a hot water bath at 70° C. for 1 hour, cooled to room temperature, and poured into ice water to decompose the excess PBr3. The oily layer was separated out and the aqueous layer was extracted with chloroform. The oily layers were combined and washed with water. The chloroform was distilled off the washed mixture. The oily residue was distilled in a vacuum (b.p. 97° C./14 mmHg) to yield 180 g (0.88 mol) of 4-propyl-1-bromocyclohexane. reached about 80° C cooled to room temperature The oily layer was separated out the aqueous layer was extracted with chloroform washed with water The chloroform was distilled off the washed mixture The oily residue was distilled in a vacuum (b.p. 97° C./14 mmHg)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 142 g (1.0 mol) of trans-4-propylcyclohexanol was stirred at room temperature and 136 g (0.5 mol) of PBr3 was added drop-wise. The reaction was exothermic and reached about 80° C. The product of the reaction was stirred over a hot water bath at 70° C. for 1 hour, cooled to room temperature, and poured into ice water to decompose the excess PBr3. The oily layer was separated out and the aqueous layer was extracted with chloroform. The oily layers were combined and washed with water. The chloroform was distilled off the washed mixture. The oily residue was distilled in a vacuum (b.p. 97° C./14 mmHg) to yield 180 g (0.88 mol) of 4-propyl-1-bromocyclohexane. reached about 80° C cooled to room temperature The oily layer was separated out the aqueous layer was extracted with chloroform washed with water The chloroform was distilled off the washed mixture The oily residue was distilled in a vacuum (b.p. 97° C./14 mmHg)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 142 g (1.0 mol) of trans-4-propylcyclohexanol was stirred at room temperature and 136 g (0.5 mol) of PBr3 was added drop-wise. The reaction was exothermic and reached about 80° C. The product of the reaction was stirred over a hot water bath at 70° C. for 1 hour, cooled to room temperature, and poured into ice water to decompose the excess PBr3. The oily layer was separated out and the aqueous layer was extracted with chloroform. The oily layers were combined and washed with water. The chloroform was distilled off the washed mixture. The oily residue was distilled in a vacuum (b.p. 97° C./14 mmHg) to yield 180 g (0.88 mol) of 4-propyl-1-bromocyclohexane. reached about 80° C cooled to room temperature The oily layer was separated out the aqueous layer was extracted with chloroform washed with water The chloroform was distilled off the washed mixture The oily residue was distilled in a vacuum (b.p. 97° C./14 mmHg)

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

Procedure: 31 g (1.35 mol) of sodium was dissolved in 660 cm3 of anhydrous ethanol, after which 216 g (1.35 mol) of diethyl malonate and then 180 g (0.88 mol) of 4-propylbromocyclohexane were added in single additions, and it was refluxed for 10 hours on a hot water bath. The reactant was cooled to room temperature, and after filtering the NaBr crystals that had formed, the ethanol in the filtrate was removed. Water was added to the residue, it was extracted with chloroform, and washed with water. The chloroform was removed, and the remaining oily substance was distilled under reduced pressure (b. p. 138° C./1.4 mmHg) to obtain 108 g (0.38 mol) of diethyl 4-propylcyclohexylmalonate (trans-cis form mixture). was refluxed for 10 hours on a hot water bath after filtering the NaBr crystals that had formed the ethanol in the filtrate was removed Water was added to the residue, it was extracted with chloroform washed with water The chloroform was removed the remaining oily substance was distilled under reduced pressure (b. p. 138° C./1.4 mmHg)

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

Procedure: 142 g (1.0 mol) of 4-propylcyclohexanol (trans-cis form mixture) was given drop addition of 136 g (0.5 mol) of PBr3 while stirring at room temperature, and heated to about 80° C. The reactant was stirred for 1 hour on a 70° C. hot water bath, then cooled to room temperature and poured into ice water to decompose the excess PBr3. The oily layer was taken off, and the water layer was extracted with chloroform, combined with the oily layer and washed with water. The chloroform was removed, and the remaining oily substance was distilled under reduced pressure (b. p. 97° C./14 mmHg) to obtain 180 g (0.88 mol) of 4-propylbromocyclohexane (trans-cis form mixture). heated to about 80° C The reactant was stirred for 1 hour on a 70° C. hot water bath cooled to room temperature the water layer was extracted with chloroform washed with water The chloroform was removed the remaining oily substance was distilled under reduced pressure (b. p. 97° C./14 mmHg)