Vanillin → HCID 86605742, compound

HRID 2221646Notes

Reaction equation

HRID 2221646 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[O:6][C:7]=1[CH3:8].[O:17]=[CH:18][C:19]1[CH:27]=[CH:26][C:24]([OH:25])=[C:21]([O:22][CH3:23])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:18]([C:19]1[CH:27]=[CH:26][C:24]([O:25][CH2:2][C:3]2[N:4]=[C:5]([C:9]3[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=3)[C:12]#[N:13])[O:6][C:7]=2[CH3:8])=[C:21]([O:22][CH3:23])[CH:20]=1)=[O:17]

Participants

6

Reactant 4

HCID 1183VanillinHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23076531HCID 23076531, compound

Product 1

HCID 86605742HCID 86605742, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-(4-chloromethyl-5-methyl-1,3-oxazol-2-yl)benzonitrile (26.3 g), vanillin (17.19 g), anhydrous potassium carbonate (15.62 g) and N,N-dimethylformamide (300 mL) was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the precipitated crystals were collected by filtration to give 3-{4-[(4-formyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzonitrile as colorless crystals (33.9 g, yield 86%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 166-167° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-7e76cf3c176c44b68b6983377071cef4
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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