Vanillin → HCID 21840251, compound

HRID 1584328Notes

Reaction equation

HRID 1584328 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][CH:7]=1.[CH3:14][O:15][C:16]1[CH:21]=[C:20]([CH:22]=[O:23])[CH:19]=[CH:18][C:17]=1[OH:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:14][O:15][C:16]1[CH:21]=[C:20]([CH:19]=[CH:18][C:17]=1[O:24][CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][CH:7]=1)[CH:22]=[O:23]

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 35511964-(Chloromethyl)-2-phenyl-1,3-oxazole

Product 1

HCID 21840251HCID 21840251, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloromethyl-2-phenyloxazole (10.0 g), vaniline (7.9 g), potassium carbonate (8.6 g) and N,N-dimethylformamide (DMF) (90 ml) was stirred for 2 hours at 100° C. The reaction mixture was poured into ice-water. Resulting crystalline precipitate was collected by filtration, which was dissolved in chloroform (400 ml). The chloroform layer was washed with water, dried (MgSO4) and concentrated. Residual crystalline product was collected by filtration to yield 3-methoxy-4-(2-phenyl-4-oxazolylmethoxy)benzaldehyde (15.4 g, 97%), which was recrystallized from ethyl acetate-hexane to give colorless prisms, m.p.119-120° C.

Workup

  1. filtrationResulting crystalline precipitate was collected by filtration, which
  2. dissolutionwas dissolved in chloroform (400 ml)
  3. washThe chloroform layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. filtrationResidual crystalline product was collected by filtration

Sources & evidence

ORD record
ord-f0f231f3292c49d8b3beb0b977eb9a87
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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