4-methoxycyclohexan-1-ol

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: A mixture of 100 g 4-methoxyphenol and Nishimura's catalyst in 750 ml ethanol were hydrogenated (50 psi hydrogen) at room temperature for 4.5 hours. The mixture was filtered and the filtrate was concentrated. at room temperature for 4.5 hours The mixture was filtered the filtrate was concentrated

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

Procedure: 4-Methoxyphenol (100 g) in ethanol (759 ml) was hydrogenated under 50 psi hydrogen using Nishimura catalyst (10.0 g) at rt for 4.5 h. The catalyst was filtered off; the solvent was removed in vacuo to yield the desired product as 95% pure yellowish liquid. at rt for 4.5 h The catalyst was filtered off the solvent was removed in vacuo

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: Following the procedure of J. Org. Chem., 28 1923 (1963), 13.35 g of AlCl3 and 125 ml of ether were stirred under N2. 25 ml of 1M LiAlH4 in ether were added by syringe to the solution. Next, 13 g of 4-methoxycyclohexanol in 50 ml of ether were added to the stirred mixture over a 30 minute period. The mixture was then allowed to settle. The supernate was removed. The solid remaining was washed three times with 25, 50 and 50 ml portions of ether. The solid precipitate was filtered and the filter cake thoroughly washed with ether. (The filtrate, and washings contained trans-4-methoxycyclohexanol). The dried precipitate (19.17 g) was slurried in 100 ml of ether. 100 ml of 10% sulfuric acid were slowly added thereto (30 minutes). The cis isomer obtained from the decompositions of the AlCl2 complex was in the ether layer which was separated. The separated layer was washed successively with 100 ml water, 50 ml saturated aqueous sodium bicarbonate and 50 ml of brine. The ethereal solution was dried and the ether evaporated to yield 1.7 g of cis-4-methoxycyclohexanol. An additional 4 g were obtained from the water layer. The supernate was removed The solid remaining was washed three times with 25, 50 and 50 ml portions of ether The solid precipitate was filtered the filter cake thoroughly washed with ether 100 ml of 10% sulfuric acid were slowly added (30 minutes) The cis isomer obtained from the decompositions of the AlCl2 complex was separated The separated layer was washed successively with 100 ml water, 50 ml saturated aqueous sodium bicarbonate and 50 ml of brine The ethereal solution was dried the ether evaporated

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

Procedure: Following the procedure of J. Org. Chem., 28 1923 (1963), 13.35 g of AlCl3 and 125 ml of ether were stirred under N2 25 ml of lM LiAlH4 in ether were added by syringe to the solution. Next, 13 g of 4-methoxycyclohexanol in 50 ml of ether were added to the stirred mixture over a 30 minute period. The mixture was then allowed to settle. The supernate was removed. The solid remaining was washed three times with 25, 50 and 50 ml portions of ether. The solid precipitate was filtered and the filter cake thoroughly washed with ether. (The filtrate, and washings contained trans-4-methoxycyclohexanol). The dried precipitate (19.17 g) was slurried in 100 ml of ether. 100 ml of 10% sulfuric acid were slowly added thereto (30 minutes). The cis isomer obtained from the decompositions of the AlCl2 complex was in the ether layer which was separated. The separated layer was washed successively with 100 ml water, 50 ml saturated aqueous sodium bicarbonate and 50 ml of brine. The ethereal solution was dried and the ether evaporated to yield 1.7 g of cis-4-methoxycyclo-hexanol. An additional 4 g were obtained from the water layer. were added by syringe to the solution The supernate was removed The solid remaining was washed three times with 25, 50 and 50 ml portions of ether The solid precipitate was filtered the filter cake thoroughly washed with ether 100 ml of 10% sulfuric acid were slowly added (30 minutes) The cis isomer obtained from the decompositions of the AlCl2 complex was separated The separated layer was washed successively with 100 ml water, 50 ml saturated aqueous sodium bicarbonate and 50 ml of brine The ethereal solution was dried the ether evaporated

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

Procedure: Following the procedure of J. Org. Chem., 28 1923 (1963), 13.35 g of AlCl3 and 125 ml of ether were stirred under N2. 25 ml of 1M LiAlH4 in ether were added by syringe to the solution. Next, 13 g of 4-methoxycyclohexanol in 50 ml of ether were added to the stirred mixture over a 30 minute period. The mixture was then allowed to settle. The supernate was removed. The solid remaining was washed three times with 25, 50 and 50 ml portions of ether. The solid precipitate was filtered and the filter cake thoroughly washed with ether. (The filtrate, and washings contained trans-4-methoxycyclohexanol). The dried precipitate (19.17 g) was slurried in 100 ml of ether. 100 ml of 10% sulfuric acid were slowly added thereto (30 minutes). The cis isomer obtained from the decompositions of the AlCl2 complex was in the ether layer which was separated. The separated layer was washed successively with 100 ml water, 50 ml saturated aqueous sodium bicarbonate and 50 ml of brine. The ethereal solution was dried and the ether evaporated to yield 1.7 g of cis-4-methoxycyclohexanol. An additional 4 g were obtained from the water layer. The supernate was removed The solid remaining was washed three times with 25, 50 and 50 ml portions of ether The solid precipitate was filtered the filter cake thoroughly washed with ether 100 ml of 10% sulfuric acid were slowly added (30 minutes) The cis isomer obtained from the decompositions of the AlCl2 complex was separated The separated layer was washed successively with 100 ml water, 50 ml saturated aqueous sodium bicarbonate and 50 ml of brine The ethereal solution was dried the ether evaporated

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

Procedure: Following the procedure of J. Org. Chem., 28 1923 (1963), 13.35 g of AlCl3 and 125 ml of ether were stirred under N2. 25 ml of 1M LiAlH4 in ether were added by syringe to the solution. Next, 13 g of 4-methoxycyclohexanol in 50 ml of ether were added to the stirred mixture over a 30 minute period. The mixture was then allowed to settle. The supernate was removed. The solid remaining was washed three times with 25, 50 and 50 ml portions of ether. The solid precipitate was filtered and the filter cake thoroughly washed with ether. (The filtrate, and washings contained trans-4-methoxycyclohexanol). The dried precipitate (19.17 g) was slurried in 100 ml of ether. 100 ml of 10% sulfuric acid were slowly added thereto (30 minutes). The cis isomer obtained from the decompositions of the AlCl2 complex was in the ether layer which was separated. The separated layer was washed successively with 100 ml water, 50 ml saturated aqueous sodium bicarbonate and 50 ml of brine. The ethereal solution was dried and the ether evaporated to yield 1.7 g of cis-4-methoxycyclohexanol. An additional 4 g were obtained from the water layer. The supernate was removed The solid remaining was washed three times with 25, 50 and 50 ml portions of ether The solid precipitate was filtered the filter cake thoroughly washed with ether 100 ml of 10% sulfuric acid were slowly added (30 minutes) The cis isomer obtained from the decompositions of the AlCl2 complex was separated The separated layer was washed successively with 100 ml water, 50 ml saturated aqueous sodium bicarbonate and 50 ml of brine The ethereal solution was dried the ether evaporated

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

Procedure: To methylene chloride there was added 11 g of pyridinium chlorochromate, and a solution consisting of 4.2 g of 4-methoxycyclohexanol and 30 ml of methylene chloride was then added. The reaction was carried out at room temperature for 3 hours. The product was purified on Florisil column. After distillation, there was obtained 3.7 g of 4-methoxycyclohexanone. was then added The product was purified on Florisil column After distillation