Vanillin → HCID 86605719, compound

HRID 2221582Notes

Reaction equation

HRID 2221582 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[O:13][C:14]([CH3:19])=[C:15]([CH2:17]Cl)[N:16]=2)[CH:7]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[O:26]=[CH:27][C:28]1[CH:36]=[CH:35][C:33]([OH:34])=[C:30]([O:31][CH3:32])[CH:29]=1.CN(C)C=O>O>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[O:13][C:14]([CH3:19])=[C:15]([CH2:17][O:34][C:33]3[CH:35]=[CH:36][C:28]([CH:27]=[O:26])=[CH:29][C:30]=3[O:31][CH3:32])[N:16]=2)[CH:7]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 1183VanillinHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23076453HCID 23076453, compound

Product 1

HCID 86605719HCID 86605719, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-(4-chloromethyl-5-methyl-1,3-oxazol-2-yl)phenyl methanesulfonate (8.35 g), potassium carbonate (3.65 g), vanillin (4.02 g) and N,N-dimethylformamide (100 mL) was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 3-{4-[(4-formyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenyl methanesulfonate as colorless crystals (7.95 g, 72%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 136-137° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab92786a81b24166b2f3796f213f131c
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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