Ethanol → 3-[N-(3,5-di-tertiary-butyl-4-hydroxyphenyl)-4-aminophenyl]propionic acid

HRID 36734Notes

Reaction equation

HRID 36734 reaction equation
[C:1]([C:5]1[C:6](=[O:27])[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:8][C:9](=[N:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(O)C.[H][H]>[Pd].CCCCCC>[C:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:14][CH:13]=2)[CH:8]=[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:6]=1[OH:27])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 702EthanolHCID 224015783-[4-(2,6-Di-tertiary-butylcyclohexadienon-4-ylideneamino)phenyl]propionic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 139604023-[N-(3,5-di-tertiary-butyl-4-hydroxyphenyl)-4-aminophenyl]propionic acidYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8058HexaneSolvent

Procedure

A mixture of 4.0 g of 3-[4-(2,6-di-tertiary-butylcyclohexadienon-4-ylideneamino)phenyl]propionic acid, 200 ml of ethanol of 0.1 g of 10% palladium on charcoal catalyst was placed on a Paar apparatus. Hydrogen uptake was complete after 30 minutes. Under a nitrogen atmosphere, the reaction mixture was filtered to remove catalyst. The filtrate was evaporated to give an oil which was coevaporated with hexane to remove all traces of ethanol and then triturated with hexane to give a light orange crystalline solid. This solid was recrystallized from a mixture of ethanol and water to give 3.1 g 3-[N-(3,5-di-tertiary-butyl-4-hydroxyphenyl)-4-aminophenyl]propionic acid, m.p. 140°-142° C. Analysis: Calculated for C23H31NO3 : % C, 74.8; % H, 8.5; % N, 3.8; Found: % C, 74.7; % H, 8.3; % N, 3.9.

Workup

  1. filtrationUnder a nitrogen atmosphere, the reaction mixture was filtered
  2. customto remove catalyst
  3. customThe filtrate was evaporated
  4. customto give an oil which
  5. customto remove all traces of ethanol
  6. customtriturated with hexane
  7. customto give a light orange crystalline solid
  8. customThis solid was recrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-8b698c4b76d74d28b7af3c1f9284ffad
Source dataset
uspto-grants-1995_05
Patent number
US05416113

Reaction notes

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