Ethyl 4-hydroxy-3-methoxybenzoate Chemical Properties

Melting point:

43-45°C

Boiling point:

108-110 °C (2 mmHg)

Density 

1.2166 (rough estimate)

refractive index 

1.5430 (estimate)

Flash point:

293°C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

8.36±0.18(Predicted)

form 

Solid

color 

White to Off-White

Odor

at 100.00 %. phenolic burnt guaiacol smoky powdery metallic

Odor Type

phenolic

BRN 

2100025

InChIKey

MWAYRGBWOVHDDZ-UHFFFAOYSA-N

LogP

2.741 (est)

CAS DataBase Reference

617-05-0(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 4-hydroxy-3-methoxy-, ethyl ester(617-05-0)

EPA Substance Registry System

Benzoic acid, 4-hydroxy-3-methoxy-, ethyl ester (617-05-0)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-24/25-26

WGK Germany 

3

RTECS 

YW5425000

TSCA 

Yes

HS Code 

29189900

MSDS

• Language:English Provider:ALFA

Ethyl 4-hydroxy-3-methoxybenzoate Usage And Synthesis

Chemical Properties

Solid. Insoluble in water; soluble in alcohol and ether.

Uses

Food preservative, medicine, sunburn preventive.

Definition

ChEBI: Ethyl vanillate is a methoxybenzoic acid.

Synthesis

Synthesis of ethyl 4-hydroxy-3-methoxybenzoate: In a round-bottomed flask equipped with a nitrogen inlet and a magnetic stirrer, a solution of vanillic acid (10 g, 59.49 mmol) in anhydrous ethanol (400 mL) was added. Concentrated hydrochloric acid (600 mg, 6.11 mmol) was slowly added to the above solution, followed by dropwise addition of concentrated sulfuric acid. The reaction mixture was stirred under reflux conditions for 48 hours. After completion of the reaction, the solvent was removed using a rotary evaporator. Deionized water (100 mL) was added to the residue, and the green oily material was separated and discarded through a partition funnel. The resulting product was dried under vacuum to afford ethyl 4-hydroxy-3-methoxybenzoate (11.45 g, 98% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.62 (dd, J = 8.5, 2.1 Hz, 1H), 7.53 (d, J = 1.8 Hz, 1H), 6.91 (d, J = 8.6 Hz, 1H), 4.33 (q, J = 7.1 Hz, 2H), 3.91 (s, 3H), 1.36 (t, J = 7.3 Hz, 3H). Hz, 3H).HPLC-MS analysis showed the expected molecular ion peak m/z 197 (MH+) and measured m/z 197.

References

[1] Patent: WO2017/62804, 2017, A1. Location in patent: Paragraph 0070
[2] Patent: WO2018/144900, 2018, A1. Location in patent: Page/Page column 47-48
[3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 13, p. 4279 - 4290
[4] Chemische Berichte, 1877, vol. 10, p. 60 Anm.
[5] Molecular crystals and liquid crystals, 1982, vol. 99, # 1-4, p. 279 - 284

Ethyl 4-hydroxy-3-methoxybenzoate(617-05-0)Related Product Information

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