3,5-Di-tert-butyl-4-hydroxybenzaldehyde → HCID 136209527, compound

HRID 1165161Notes

Reaction equation

HRID 1165161 reaction equation
Cl.[NH2:2][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:8][CH2:9][CH3:10].[OH:11][C:12]1[C:19]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=1[C:24]([CH3:27])([CH3:26])[CH3:25]>C(O)C>[OH:11][C:12]1[C:19]([C:20]([CH3:22])([CH3:21])[CH3:23])=[CH:18][C:15]([CH:16]=[N:2][N:3]2[CH:7]=[CH:6][N:5]=[C:4]2[CH2:8][CH2:9][CH3:10])=[CH:14][C:13]=1[C:24]([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 19862551HCID 19862551, compound

Product 1

HCID 136209527HCID 136209527, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.47 g of 1-amino-2-propylimidazole hydrochloride are dissolved in 300 ml of ethanol, and 3.5 g of 4-hydroxy-3,5-di-tert.-butylbenzaldehyde are added. The mixture is stirred at room temperature for 3 hours and the solution obtained is evaporated. The residue is treated with 150 ml of water and 150 ml of methylene chloride, and saturated sodium bicarbonate solution is added while stirring up to a neutral reaction (pH=7). The methylene chloride phase is separated. The aqueous phase is extracted once with 50 ml of methylene chloride. The methylene chloride solutions are combined, dried and evaporated. The residue is triturated with ether, and the solid is removed by filtration and dried at 60° in a vacuum. There is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)-2-propylimidazole of m.p. 160°-161°.

Workup

  1. customthe solution obtained
  2. customis evaporated
  3. additionThe residue is treated with 150 ml of water and 150 ml of methylene chloride, and saturated sodium bicarbonate solution
  4. additionis added
  5. stirringwhile stirring up to a neutral reaction (pH=7)
  6. customThe methylene chloride phase is separated
  7. extractionThe aqueous phase is extracted once with 50 ml of methylene chloride
  8. customdried
  9. customevaporated
  10. customThe residue is triturated with ether
  11. customthe solid is removed by filtration
  12. customdried at 60° in a vacuum

Sources & evidence

ORD record
ord-e9f9cf2c96764fd896adc7520b57e273
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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