HCID 22925713, compound → HCID 178426060, compound

HRID 985751Notes

Reaction equation

HRID 985751 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH3:21])[CH:15]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>CO>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:9][CH2:10][C@H:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([CH3:21])[CH:15]=3)[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 22925713HCID 22925713, compound

Product 1

HCID 178426060HCID 178426060, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of 4-(4′-(4″-hydroxyphenyl)cyclohexyl)-2-methyl-1-hydroxybenzene obtained in Example 1 was dissolved in 10 g of methanol at room temperature. The solution was injected into a preparative high performance liquid chromatography to carry out separation of cis- and trans-isomers (solvent: 60% aqueous solution of methanol; time: 40 minutes). As a result, about 50 mg of 4-(trans-4′-(4″-hydroxyphenyl)cyclohexyl)-2-methyl-1-hydroxybenzene was obtained as white crystals with a retention time of 17.6 minutes. It was found to have a purity of 99% and a melting point of 214° C. (DTA method). Furthermore, about 100 mg of 4-(cis-4′-(4″-hydroxyphenyl)cyclohexyl)-2-methyl-1-hydroxybenzene was obtained as pale yellow oily substance with a retention time of 28.2 minutes. It was found to have a purity of 99%.

Workup

  1. customseparation of cis- and trans-isomers (solvent: 60% aqueous solution of methanol; time: 40 minutes)

Sources & evidence

ORD record
ord-d259fd608b4049968ee5ecc200381f7f
Source dataset
uspto-grants-2005_03
Patent number
US06872858B2

Reaction notes

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