Boron trifluoride etherate → 3-[4-(2,6-Di-tertiary-butylcyclohexadienon-4-ylideneamino)phenyl]propionic acid

HRID 36733

Reaction equation

HRID 36733 reaction equation
[C:1]([C:5]1[C:6](=[O:16])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:9](=O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:20][CH:19]=1.B(F)(F)F.CCOCC>O1CCCC1>[C:1]([C:5]1[C:6](=[O:16])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:9](=[N:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:22][CH:23]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 128672,6-Di-t-butyl-p-benzoquinoneHCID 754513-(4-Aminophenyl)propionic acid

Product 1

HCID 224015783-[4-(2,6-Di-tertiary-butylcyclohexadienon-4-ylideneamino)phenyl]propionic acidYield 55.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.51 g (0.025 mole) of 2,6-di-tertiary-butyl-p-benzoquinone, 4.54 g (0.027 mole) of 3-(4-aminophenyl)propionic acid, 50 ml of tetrahydrofuran and 0.25 ml of boron trifluoride etherate was heated on a steam cone under a slow stream of nitrogen for two hours. The resulting solid was triturated with hexane, collected, rinsed with hexane and recrystallized from a mixture of ethyl acetate and hexane to give 5.1 g yellow 3-[4-(2,6-di-tertiary-butylcyclohexadienon-4-ylideneamino)phenyl]propionic acid, m.p. 165°-167° C. Analysis: Calculated for C23H29NO3 : % C, 75.2; % H, 8.0; % N, 3.8; Found % C, 74.8; % H, 7.9; % N, 3.7.

Workup

  1. temperaturewas heated on a steam cone under a slow stream of nitrogen for two hours
  2. customThe resulting solid was triturated with hexane
  3. customcollected
  4. washrinsed with hexane
  5. customrecrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-beb8cdbc108c49f395f070dc7c7012a6
Source dataset
uspto-grants-1995_05
Patent number
US05416113

Linked notes

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