Phenol → HCID 54083278, compound

HRID 1419845Notes

Reaction equation

HRID 1419845 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>C1C=CC=CC=1.CCOC(C)=O>[O:7]([C:23]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:24])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 682631,1'-CarbonyldiimidazoleHCID 450368384-[(Piperidin-4-yl)oxy]benzaldehyde

Product 1

HCID 54083278HCID 54083278, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of phenol (0.83 g) and 4-(piperidin-4-yloxy)benzaldehyde (2 g) in dry benzene (20 ml), 1,1'-carbonyldiimidazole (1.58 g) was added and the reaction mixture was stirred at 80° C. for 12 h. At the end of this time, the reaction mixture was diluted with EtOAc, washed with H2O, dried (Na2SO4) and the solvent was removed under reduced pressure. The crude product was chromatographed on silica gel using 5 to 15% (gradient elution) ethyl acetate in petroleum ether to afford 1.9 g (61%) of the title compound.

Workup

  1. additionwas added
  2. washwashed with H2O
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was chromatographed on silica gel using 5 to 15% (gradient elution) ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-810c593c88dc4a6a90e93fded4785bfd
Source dataset
uspto-grants-1999_03
Patent number
US05889025

Reaction notes

Loading…