HCID 22508141, compound → HCID 22925721, compound

HRID 985752Notes

Reaction equation

HRID 985752 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[CH2:14][CH:13]=2)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>[Ni].C(O)(C)C>[OH:24][C:21]1[CH:22]=[CH:23][C:18]([CH:15]2[CH2:14][CH2:13][CH:12]([C:7]3[CH:8]=[CH:9][C:10]([OH:11])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=3)[CH2:17][CH2:16]2)=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 22508141HCID 22508141, compound

Product 1

HCID 22925721HCID 22925721, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

26.6 g (0.081 mol) of 1-(3-t-butyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)-1-cyclohexene obtained in Example 4 of Example A, 266 g of isopropyl alcohol and 5.5 g of Raney nickel catalyst were placed in a reaction vessel (1L capacity autoclave), and then in the same manner as in Example 3, 26.6 g of 4-(4′-(4″-hydroxyphenyl)-cyclohexyl)-2-t-butyl-1-hydroxybenzene was obtained as white crystals having a purity of 97.9% (high performance liquid chromatography). The yield was found to be 99.2 mol % based on the 1-(3-t-butyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)-1-cyclohexene. The selectivity of trans-/cis-isomers of 4-(4′-(4″-hydroxyphenyl)cyclohexyl)-2-t-butyl-1-hydroxybenzene was found to be 64/36 (high performance liquid chromatography).

Sources & evidence

ORD record
ord-cb6e822d2e8941a9b65c3b6f3eef0d33
Source dataset
uspto-grants-2005_03
Patent number
US06872858B2

Reaction notes

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