3,5-Di-tert-butyl-4-hydroxybenzaldehyde → HCID 136199534, compound

HRID 1165159Notes

Reaction equation

HRID 1165159 reaction equation
Cl.[NH2:2][N:3]1[CH:7]=[C:6]([CH3:8])[N:5]=[CH:4]1.[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]=[C:6]([CH3:8])[N:5]=[CH:4]2)=[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 19862539HCID 19862539, compound

Product 1

HCID 136199534HCID 136199534, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.5 g of 1-amino-4-methylimidazole hydrochloride are dissolved in 200 ml of ethanol. 6.2 g of 4-hydroxy-3,5-di-tert.-butylbenzaldehyde are added and the mixture is stirred at room temperature overnight. The solution obtained is then evaporated in a vacuum. The residue is treated with 150 ml of methylene chloride and 150 ml of water, stirred and saturated sodium bicarbonate solution is added up to a neutral reaction (pH=7). The methylene chloride phase is separated and the aqueous phase is extracted with 50 ml of methylene chloride. The methylene chloride phases are combined, washed once with 10% sodium chloride solution, dried and evaporated. The residue is triturated with cold ether. The solid is removed by filtration, washed with ether and n-hexane and dried at 70° in a vacuum. There is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)-4-methylimidazole of m.p. 150°-151°.

Workup

  1. customThe solution obtained
  2. customis then evaporated in a vacuum
  3. additionThe residue is treated with 150 ml of methylene chloride and 150 ml of water
  4. stirringstirred
  5. additionsaturated sodium bicarbonate solution is added up to a neutral reaction (pH=7)
  6. customThe methylene chloride phase is separated
  7. extractionthe aqueous phase is extracted with 50 ml of methylene chloride
  8. washwashed once with 10% sodium chloride solution
  9. customdried
  10. customevaporated
  11. customThe residue is triturated with cold ether
  12. customThe solid is removed by filtration
  13. washwashed with ether and n-hexane
  14. customdried at 70° in a vacuum

Sources & evidence

ORD record
ord-b83d72fe000744c1b30108784b89130f
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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