Vanillyl ethyl ether Chemical Properties

Boiling point:

125°C/4mmHg(lit.)

Density 

1.087±0.06 g/cm3(Predicted)

refractive index 

1.5280 to 1.5320

FEMA 

3815 | VANILLYL ETHYL ETHER

storage temp. 

Inert atmosphere,Room Temperature

form 

clear liquid

pka

9.73±0.20(Predicted)

color 

Colorless to Almost colorless

Odor

at 20.00 % in ethyl alcohol. alcoholic rum sweet chocolate creamy vanilla spicy nutmeg smoky

Odor Type

chocolate

JECFA Number

887

LogP

1.46

CAS DataBase Reference

13184-86-6

NIST Chemistry Reference

Phenol, 4-(ethoxymethyl)-2-methoxy-(13184-86-6)

EPA Substance Registry System

Phenol, 4-(ethoxymethyl)-2-methoxy- (13184-86-6)

Safety Information

TSCA 

TSCA listed

HS Code 

2909500090

Vanillyl ethyl ether Usage And Synthesis

Chemical Properties

Vanillyl ethyl ether has a phenolic, smoky odor and a strong, pungent taste.

Occurrence

Reportedly present in grape brandy (cognac), rum, whiskey and vanilla.

Uses

flavors and fragrances

Definition

ChEBI: 4-(Ethoxymethyl)-2-methoxyphenol is a member of phenols and a member of methoxybenzenes.

Preparation

In a patented process, prepared by the reaction of cyclodextrin or branched-cyclodextrin with vanillyl alcohol.

Synthesis

General procedure for the synthesis of vanillyl ethyl ether from vanillin and triethyl orthoformate: 3.04 g (20.0 mmol) of vanillin, 5.93 g (40.0 mmol) of triethyl orthoformate, 15.0 mg of p-toluenesulphonic acid monohydrate, and 15.0 mg 5% palladium-carbon catalyst were added to a 100 ml autoclave (equipped with an inner tube). After displacing the internal gas of the system under nitrogen protection, it was replaced with hydrogen and filled with hydrogen at 3.0 MPa. The autoclave temperature was controlled at 130°C and the reaction was continuously stirred for 1 hour. Upon completion of the reaction, the reaction mixture was cooled and the hydrogen pressure was subsequently released. The palladium carbon catalyst was removed by filtration and the unreacted triethyl orthoformate was recovered by distillation under reduced pressure, resulting in 3.60 g of vanillyl ethyl ether (97.4% purity and 96.2% yield as determined by internal standard method). The structure of the product was confirmed by 1H-NMR (CDCl3): δ=1.37 (3H, t), 3.42 (1H, q), 3.86 (3H, s), 4.44 (2H, s), 5.92 (1H, s), 6.88 (3H, m).

References

[1] Patent: EP2813482, 2014, A1. Location in patent: Paragraph 0139; 0140

Vanillyl ethyl ether(13184-86-6)Related Product Information

• Trinexapac-ethyl
• 2-Ethoxyethanol
• Vanillyl alcohol
• Ethylparaben
• Ethyl acetate
• ISOXADIFEN-ETHYL
• m-Cresol
• p-(2-Methoxyethyl) phenol
• Ethanol
• Guaiacol
• 2-Ethoxyphenol
• Ethylbenzene
• Dimethyl ether
• 3-Trifluoromethylphenol
• 4-Methoxyphenol
• Boron trifluoride diethyl etherate
• p-Cresol
• 4-Ethoxyphenol