Diethyl Ether → 3-[4-(1,1-Dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenol

HRID 1074475Notes

Reaction equation

[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[CH:17]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CCOCC.[H-].C([Al+]CC(C)C)C(C)C>O>[CH3:9][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:21][CH2:20][CH2:19][CH:18]([OH:22])[CH:17]=2)=[C:12]([OH:23])[CH:11]=1)([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Conditions

Temperature: -30 °C

Procedure

To a -30° C. solution of 1.00 g. (3.18 mmole) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-2-cyclohexenone in 60 ml. of ether was added dropwise 6.3 ml. of a 1 M (in toluene) diisobutylaluminum hydride solution. The reaction was stirred 30 min. longer at -30° C. and then added to 1.5 l. water. The quenched solution was extracted with three 400 ml. portions of ether and the combined extracts washed twice with 125 ml. of saturated sodium chloride and dried over magnesium sulfate. After evaporation the crude product was purified via column chromatography on 50 g. of florial eluted with ether to yield an oil. Crystallization of the oil from pentane gave 256 mg. (25%) of the title product.

Workup

customTo a -30° C.
additionadded to 1.5 l
extractionThe quenched solution was extracted with three 400 ml
washportions of ether and the combined extracts washed twice with 125 ml
dry with materialof saturated sodium chloride and dried over magnesium sulfate
customAfter evaporation the crude product
customwas purified via column chromatography on 50 g
washof florial eluted with ether
customto yield an oil
customCrystallization of the oil from pentane
customgave 256 mg

Sources & evidence

ORD record: ord-b82452f557b84f9d91f117af8fca164c
Source dataset: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04391827

Reaction notes

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