HCID 54182980, compound → HCID 19003369, compound

HRID 2259327Notes

Reaction equation

HRID 2259327 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:13][CH:14]=[CH:15][CH2:16][C:17]2[CH:22]=[C:21]([CH3:23])[C:20]([OH:24])=[C:19]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:18]=2)[CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:25]([C:19]1[CH:18]=[C: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:22]=[C:21]([CH3:23])[C:20]=1[OH:24])([CH3:26])([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 54182980HCID 54182980, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19003369HCID 19003369, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

8.55 g (22.5 mmol) of 1,4-bis(3'-tert-butyl-5'-methyl-4'-hydroxyphenyl)but-2-ene in 100 ml of ethyl acetate are hydrogenated over 1 g of Pd/C (5%) at room temperature under atmospheric pressure. After 30 minutes, the uptake of hydrogen has ended. The reaction mixture is filtered over Celite and the resulting filtrate is concentrated. Crystallization of the crude product from acetonitrile gives 6.6 g (77% of theory) of 1,4-bis(3'-tert-butyl-5'-methyl-4'-hydroxyphenyl)butane of melting point 106°-107° C.

Workup

  1. filtrationThe reaction mixture is filtered over Celite
  2. concentrationthe resulting filtrate is concentrated
  3. customCrystallization of the crude product from acetonitrile

Sources & evidence

ORD record
ord-14890cf8d1f74e97a4f34165903d766e
Source dataset
uspto-grants-1995_12
Patent number
US05473003

Reaction notes

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