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Vanillin → Methyl 5-{4-[(4-formyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-methylbenzoate

HRID 2221633
Notes
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Reaction equation

HRID 2221633 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([CH3:19])=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])[O:6][C:7]=1[CH3:8].[O:20]=[CH:21][C:22]1[CH:30]=[CH:29][C:27]([OH:28])=[C:24]([O:25][CH3:26])[CH:23]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:21]([C:22]1[CH:30]=[CH:29][C:27]([O:28][CH2:2][C:3]2[N:4]=[C:5]([C:9]3[CH:10]=[CH:11][C:12]([CH3:19])=[C:13]([CH:18]=3)[C:14]([O:16][CH3:17])=[O:15])[O:6][C:7]=2[CH3:8])=[C:24]([O:25][CH3:26])[CH:23]=1)=[O:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1183VanillinHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23076346HCID 23076346, compound

Product 1

HCID 86605739Methyl 5-{4-[(4-formyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-methylbenzoateYield 85.8%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 5-(4-chloromethyl-5-methyl-1,3-oxazol-2-yl)-2-methylbenzoate (1.21 g), vanillin (0.65 g), anhydrous potassium carbonate (0.59 g) and N,N-dimethylformamide (50 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 organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give methyl 5-{4-[(4-formyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-methylbenzoate as colorless crystals (1.45 g, yield 85%). 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 organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-21e9b61c55eb425981a231b5f5438f33
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07368578B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes