4-ETHOXYBENZYL ALCOHOL Chemical Properties

Melting point:

32-34 °C(lit.)

Boiling point:

273 °C(lit.)

Density 

1.0505 (rough estimate)

refractive index 

n20/D 1.535(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Solubility in methanol is almost transparent.

pka

14.54±0.10(Predicted)

form 

powder to lump to clear liquid

color 

White or Colorless to Light yellow

CAS DataBase Reference

6214-44-4(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29094990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-ETHOXYBENZYL ALCOHOL Usage And Synthesis

Chemical Properties

WHITE TO SLIGHTLY YELLOW CRYST. LOW MELTING MASS

Uses

It is used in the identification of sulfation sites of metabolites and prediction of the compounds? biological effects and in chemical investigation of Wedelia calendulacea.

Synthesis

General procedure for the synthesis of p-ethoxybenzyl alcohol from 4-ethoxybenzaldehyde: NaBH4 (0.8 g, 21.7 mmol) was added in batches to a stirring solution of 4-ethoxybenzaldehyde (3.0 g, 19.7 mmol) in methanol (50 mL) at 0 °C, and the addition process lasted for 15 minutes. After the addition, the reaction mixture was continued to be stirred at room temperature for 30 min. After completion of the reaction, the solvent was removed by rotary evaporator to obtain the crude product. The crude product was dissolved in water and extracted twice with ethyl acetate (EtOAc). The organic phases were combined, washed sequentially with water and saturated saline, and dried over anhydrous sodium sulfate. The dried organic phase was concentrated under reduced pressure to give a white solid product, p-ethoxybenzyl alcohol, in 82% yield. The product was analyzed by LC-MS showing [M+H]+ peak of 135.2. 1H-NMR (400 MHz, CDCl3) δ 7.266-7.286 (d, 2H, J = 8.0 Hz), 6.872-6.893 (d, 2H, J = 8.4 Hz), 4.609 (s, 2H), 4.010-4.061 (q, 2H, J = 6.8 Hz), 1.396-1.430 (t, 3H, J = 6.8 Hz).

References

[1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 10, p. 1694 - 1698
[2] Patent: WO2010/127208, 2010, A1. Location in patent: Page/Page column 62
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4861 - 4868
[4] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
[5] Journal of the Chemical Society, 1956, p. 2455,246

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