HCID 22508144, compound → HCID 22508118, compound

HRID 985753Notes

Reaction equation

HRID 985753 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[CH2:12][CH:11]=2)[CH:5]=[C:6]([CH3:9])[C:7]=1[OH:8]>[Ni].C(O)(C)C>[OH:22][C:19]1[CH:18]=[CH:17][C:16]([CH:13]2[CH2:12][CH2:11][CH:10]([C:4]3[CH:5]=[C:6]([CH3:9])[C:7]([OH:8])=[C:2]([CH3:1])[CH:3]=3)[CH2:15][CH2:14]2)=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 22508144HCID 22508144, compound

Product 1

HCID 22508118HCID 22508118, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 3776IsopropanolSolvent

Procedure

19.6 g (0.063 mol) of 1-(3,5-dimethyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)-1-cyclohexene obtained in Example 5 of Example A, 300 g of isopropyl alcohol and 5.2 g of Raney nickel catalyst were placed in a reaction vessel (1L capacity autoclave), and then in the same manner as in Example 3, 18.6 g of 4-(4′-(4″-hydroxyphenyl)-cyclohexyl)-2,6-dimethyl-1-hydroxybenzene) was obtained as white crystals having a purity of 92.7% (high performance liquid chromatography). The yield was found to be 92.0 mol % based on the 1-(3,5-dimethyl-4-hydroxyphenyl)-4-(4-hydroxyphenyl)-1-cyclohexene used. The selectivity of trans-/cis-isomers of 4-(4′-(4″-hydroxyphenyl)cyclohexyl)-2,6-dimethyl-1-hydroxybenzene was found to be 69/31 (high performance liquid chromatography).

Sources & evidence

ORD record
ord-c4836c04dc4d4b94bf16edb0d5499524
Source dataset
uspto-grants-2005_03
Patent number
US06872858B2

Reaction notes

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