2-Butanone, 4-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]- → HCID 21274350, compound

HRID 1439622Notes

Reaction equation

HRID 1439622 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18](=[O:20])[CH3:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Cr]([O-])([O-])=O.[Cu+2]>[C:12]([C:9]1[CH:8]=[C:7]([CH2:16][CH2:17][CH:18]([OH:20])[CH3:19])[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:10]=1[OH:11])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 1

HCID 39609622-Butanone, 4-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-

Product 1

HCID 21274350HCID 21274350, compound

Reagents, catalysts & solvents 2

HCID 178505374HCID 178505374, compoundCatalystHCID 702EthanolSolvent

Procedure

4-(3,5-di-t-butyl-4-hydroxyphenyl) butane-2-ol was prepared by catalytic hydrogenation of 84.8 grams of 4-(3,5-di-t-butyl-4-hydroxyphenyl) butane-2-one in 400 milliliters of ethanol solvent in the presence of 10 grams of copper chromite catalyst at 150° C, and 1000 pounds per square inch pressure in a one-liter autoclave. Reduction was complete in three hours. The catalyst was filtered off and the filtrate was evaporated. The residue was crystallized by the addition of hexane to yield 82.9 grams of a white solid product (97 percent yield) having a melting point between 64° C and 66° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized by the addition of hexane

Sources & evidence

ORD record
ord-3131866bdff044749097d167db71cbb1
Source dataset
uspto-grants-1977_11
Patent number
US04060556

Reaction notes

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