3,5-Di-tert-butyl-4-hydroxybenzaldehyde → HCID 136209557, compound

HRID 1165158Notes

Reaction equation

HRID 1165158 reaction equation
Cl.[NH2:2][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH:8]([CH3:10])[CH3:9].[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[CH:8]([CH3:10])[CH3:9])=[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 19862536HCID 19862536, compound

Product 1

HCID 136209557HCID 136209557, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.65 g of the above crude 1-amino-2-isopropylimidazole hydrochloride is dissolved in 30 ml of ethanol, 0.94 g of 4-hydroxy-3,5-di-tert.-butylbenzaldehyde is added and the mixture is stirred at room temperature for 2 hours. The resulting solution is evaporated in a vacuum. The residue is partitioned between methylene chloride and water. The aqueous phase is treated with sodium bicarbonate solution up to a neutral reaction (pH=7) and the methylene chloride phase is separated, dried, filtered and evaporated. The residue is stirred with ether, whereupon the solid is removed by filtration and dried; there is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)-2-isopropylimidazole of m.p. 159°-160°.

Workup

  1. customThe resulting solution is evaporated in a vacuum
  2. customThe residue is partitioned between methylene chloride and water
  3. additionThe aqueous phase is treated with sodium bicarbonate solution up to a neutral reaction (pH=7)
  4. customthe methylene chloride phase is separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. stirringThe residue is stirred with ether, whereupon the solid
  9. customis removed by filtration
  10. customdried

Sources & evidence

ORD record
ord-a717d2dc385b4e388ee1deb9d3d34e79
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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