4-Methoxycyclohexanol (cis,trans) → HCID 178496630, compound

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.

1. customThe supernate was removed
2. washThe solid remaining was washed three times with 25, 50 and 50 ml portions of ether
3. filtrationThe solid precipitate was filtered
4. washthe filter cake thoroughly washed with ether
5. addition100 ml of 10% sulfuric acid were slowly added
6. custom(30 minutes)
7. customThe cis isomer obtained from the decompositions of the AlCl2 complex
8. customwas separated
9. washThe separated layer was washed successively with 100 ml water, 50 ml saturated aqueous sodium bicarbonate and 50 ml of brine
10. customThe ethereal solution was dried
11. customthe ether evaporated

ORD record

ord-48e4b86706fc4eefaa26bb922942783d

Source dataset

uspto-grants-1990_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04914100