3,5-Di-tert-butyl-4-hydroxybenzaldehyde → HCID 136209521, compound

HRID 1165137Notes

Reaction equation

HRID 1165137 reaction equation
Cl.[NH2:2][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH3:8].[OH:9][C:10]1[C:17]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:16][C:13]([CH:14]=O)=[CH:12][C:11]=1[C:22]([CH3:25])([CH3:24])[CH3:23]>C(O)C>[OH:9][C:10]1[C:17]([C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:16][C:13]([CH:14]=[N:2][N:3]2[CH:7]=[CH:6][N:5]=[C:4]2[CH3:8])=[CH:12][C:11]=1[C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 22167428HCID 22167428, compound

Product 1

HCID 136209521HCID 136209521, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.35 g of 1-amino-2-methylimidazole hydrochloride are dissolved in 300 ml of ethanol, whereupon 9.3 g of 4-hydroxy-3,5-di-tert.-butylbenzaldehyde are added. The mixture is stirred at room temperature for 1 hour and then evaporated in a vacuum. 150 ml of ice-water and 200 ml of methylene chloride are added to the residue and the mixture is neutralized (pH=7) with saturated sodium bicarbonate solution. The methylene chloride phase is separated and the aqueous phase is extracted with 100 ml of methylene chloride. The combined methylene chloride phases are dried and evaporated. The residue is stirred with ether and filtered. The filter residue is dried at 80° in a vacuum and there is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)-2-methylimidazole of m.p. 206°-207°.

Workup

  1. additionare added
  2. customevaporated in a vacuum
  3. addition150 ml of ice-water and 200 ml of methylene chloride are added to the residue
  4. customThe methylene chloride phase is separated
  5. extractionthe aqueous phase is extracted with 100 ml of methylene chloride
  6. dry with materialThe combined methylene chloride phases are dried
  7. customevaporated
  8. stirringThe residue is stirred with ether
  9. filtrationfiltered
  10. customThe filter residue is dried at 80° in a vacuum

Sources & evidence

ORD record
ord-cfe92fcb0dc84919874f41d5373e2b77
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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