Hydrochloric Acid → HCID 54412028, compound

HRID 36736Notes

Reaction equation

HRID 36736 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:22]=[CH:21][C:15]([CH:16]=[CH:17][C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl>[Zn].CO>[C:1]([C:5]1[CH:10]=[C:9]([CH:8]=[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:6]=1[OH:27])[NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH:16]=[CH:17][C:18]([OH:20])=[O:19])=[CH:21][CH:22]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54363789HCID 54363789, compound

Product 1

HCID 54412028HCID 54412028, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.0 g of 4-(2,6-di-tertiary-butyl-cyclohexadienon-4-ylideneamino)cinnamic acid, 100 ml of methanol, 0.5 ml of concentrated hydrochloric acid and 2 g of zinc powder was stirred for ten minutes. The mixture was filtered and the filtrate was evaporated to give a yellow gummy solid. This material was recrystallized from a mixture of 15 ml of benzene, 4 ml of hexane and 2 ml of cyclohexane to give 0.4 g of yellow granular 4-(3,5-di-tertiary-butyl-4-hydroxyanilino)cinnamic acid, m.p. 199°-200° C. Analysis: Calculated for C23H29NO3 2/3C6H6 : % C, 77.4; % H, 7.9; % N, 3.3; Found: % C, 77.2; % H, 7.8; % N, 3.3.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customto give a yellow gummy solid
  4. customThis material was recrystallized from a mixture of 15 ml of benzene, 4 ml of hexane and 2 ml of cyclohexane

Sources & evidence

ORD record
ord-28405b5287564c8e9c3a1e4818e8ed1f
Source dataset
uspto-grants-1995_05
Patent number
US05416113

Reaction notes

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