3-Hydroxybenzaldehyde → 3-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzaldehyde

HRID 1740923Notes

Reaction equation

HRID 1740923 reaction equation
ClC[C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:7][CH:6]=[C:5]([CH3:8])[O:4]1.[OH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20].[C:24](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:8][C:5]1[O:4][C:3]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:7][C:6]=1[CH2:24][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 185461732-Chloromethyl-5-methyl-2-phenyloxazole

Product 1

HCID 107088433-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzaldehydeYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-chloromethyl-5-methyl-2-phenyloxazole (20.8 g), 3-hydroxybenzaldehyde (12.2 g), potassium carbonate (27.6 g) and N,N-dimethylformamide (DMF) (200 ml) was heated at 90° C. for 2 hours. The reaction mixture was poured into water, and subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate (MgSO4). The solvent was distilled off, whereby 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzaldehyde (26.5 g, 90%) was obtained. Recrystallization from ethanol gave colorless prisms. Melting point: 67-68° C.

Workup

  1. extractionsubjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over magnesium sulfate (MgSO4)
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-bc5a5ac3785c4769a94956fe8db872d9
Source dataset
uspto-grants-1999_10
Patent number
US05972970

Reaction notes

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