(4-Methoxybenzyloxy)acetic acid

(4-Methoxybenzyloxy)acetic acid Property

Melting point:

50.8-51.8 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))

Boiling point:

367.4±22.0 °C(Predicted)

Density 

1.198±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.40±0.10(Predicted)

color 

White to Off-White

Safety

HS Code 

2918999090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

(4-Methoxybenzyloxy)acetic acid Chemical Properties,Usage,Production

Synthesis

4-Methoxybenzyl alcohol (1 eq.) and bromoacetic acid (1.2 eq.) were dissolved in anhydrous tetrahydrofuran at 0 °C. Sodium hydride (60% w/w, mineral oil dispersion, 3 eq.) was added in three batches. The reaction mixture was stirred at 70 °C for 4 hours. After cooling to room temperature, water was added and the resulting mixture was washed with hexane. The aqueous phase was acidified to pH 2 with 1N hydrochloric acid and subsequently extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography with hexane solution of 50% ethyl acetate as eluent gave (4-methoxybenzyloxy)acetic acid (0.51 g, 71% yield) as a colorless solid.1H NMR (500 MHz, CDCl3) δ 7.29 (m, 2H), 6.90 (m, 2H), 4.59 (s, 2H), 4.10 (s, 2H), 3.81 ( s, 3H).

References

[1] Bioorganic and medicinal chemistry letters, 2001, vol. 11, # 21, p. 2837 - 2841
[2] Synlett, 2012, vol. 23, # 19, p. 2845 - 2849
[3] Tetrahedron Letters, 2002, vol. 43, # 41, p. 7427 - 7429
[4] Patent: WO2014/144100, 2014, A2. Location in patent: Paragraph 00274
[5] Patent: WO2006/109729, 2006, A1. Location in patent: Page/Page column 138-139