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

HRID 2254881Notes

Reaction equation

HRID 2254881 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 The filtrate
  3. customwas 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-d130951ae5ee4c21b3a6596512775528
Source dataset
uspto-grants-1993_08
Patent number
US05237070

Reaction notes

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