4-Fluorophenol → HCID 178505896, compound

HRID 2209390Notes

Reaction equation

[OH-].[K+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C1(C)C=CC(S(O[CH2:21][C@H:22]2[CH2:27][CH2:26][C@H:25]([C@H:28]3[CH2:33][CH2:32][C@H:31]([CH2:34][CH2:35][CH:36]4[O:40][CH2:39][CH2:38][O:37]4)[CH2:30][CH2:29]3)[CH2:24][CH2:23]2)(=O)=O)=CC=1>C(O)C>[O:37]1[CH2:38][CH2:39][O:40][CH:36]1[CH2:35][CH2:34][C@H:31]1[CH2:32][CH2:33][C@H:28]([C@H:25]2[CH2:26][CH2:27][C@H:22]([CH2:21][O:10][C:7]3[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=3)[CH2:23][CH2:24]2)[CH2:29][CH2:30]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 0.33 g of potassium hydroxide in 7 ml of 95 percent ethanol is treated with 1.12 g of p-fluorophenol. Thereafter, the mixture is treated with a solution of 2.26 g of [trans-4-[trans-4-(2-(1,3-dioxolan-2-yl)ethyl)cyclohexyl]cyclohexyl]methyl p-toluenesulfonate in 23 ml of ethanol and stirred at 80° C. (bath temperature) for 24 hours. Subsequently, the reaction mixture is partitioned in 1N hydrochloric acid and methylene chloride. The organic phase is washed several times with water, dried over magnesium sulfate, filtered and evaporated. Chromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether gives 1-[[trans-4-(trans-4-(2-(1,3-dioxolan-2-yl)ethyl)cyclohexyl]cyclohexyl]methoxy]-4-fluorobenzene.

Workup

customSubsequently, the reaction mixture is partitioned in 1N hydrochloric acid
washThe organic phase is washed several times with water
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customChromatographic purification of the resulting crude product on silica gel with ethyl acetate/petroleum ether

Sources & evidence

ORD record: ord-2bd38480b5ba409e85e3dc87007b9546
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05454974

Reaction notes

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