HCID 19003350, compound → HCID 19003406, compound

HRID 2259325Notes

Reaction equation

HRID 2259325 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:13](=O)[CH2:14][CH2:15][CH2:16][C:17]([C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([OH:26])=[C:21]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:20]=2)=O)[CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.S(=O)(=O)(O)O.[Pd]>[C:27]([C:21]1[CH:20]=[C:19]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:7]2[CH:8]=[C:9]([CH3:12])[C:10]([OH:11])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=2)[CH:24]=[C:23]([CH3:25])[C:22]=1[OH:26])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 2

HCID 19003350HCID 19003350, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19003406HCID 19003406, compoundYield 68.1%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

8.17 g (19 mmol) of 1,5-di(3'-tert-butyl-5'-methyl-4'-hydroxyphenyl)-1,5-pentanedione in 80 ml of ethyl acetate and 3-5 drops of concentrated sulfuric acid are hydrogenated over 1.6 g of Pd/C (5%) at room temperature under atmospheric pressure. After 12 hours, the uptake of hydrogen has ended. The catalyst is filtered over Celite and the resulting colourless solution is concentrated on a rotary evaporator. Chromatography of the liquid residue (SiO2, hexane/ethyl acetate 19:1) gives 5.13 g (67% of theory) of 1,5-bis(3'-tert-butyl-5'-methyl-4'-hydroxyphenyl)pentane as a viscous oil.

Workup

  1. filtrationThe catalyst is filtered over Celite
  2. concentrationthe resulting colourless solution is concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-33e36c6ce4144520a6c0bdea355e9986
Source dataset
uspto-grants-1995_12
Patent number
US05473003

Reaction notes

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