4-(2-methoxy-2-oxoethyl)benzoic acid

4-(2-methoxy-2-oxoethyl)benzoic acid Property

Melting point:

136 °C

Boiling point:

331.0±25.0 °C(Predicted)

Density 

1.254±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.16±0.10(Predicted)

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

4-(2-methoxy-2-oxoethyl)benzoic acid Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of methyl 4-carboxyphenylacetate from methanol and 4-(carboxymethyl)benzoic acid: to a solution of 4-(carboxymethyl)benzoic acid (1.00 g, 5.55 mmol, 1 eq.) in methanol (11 mL) was added thionyl chloride (0.020 mL, 0.28 mmol, 5 mol%). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was dissolved in methyl tertiary butyl ether (MTBE). It was washed three times sequentially with saturated NaHCO3 solution and once more with water. The bicarbonate and aqueous phase extracts were combined and acidified with 1N HCl until the monomethyl ester precipitated. The mixture was extracted three times with MTBE, the organic layers were combined and dried with anhydrous Na2SO4. Concentration of the organic layer under reduced pressure afforded 4-(2-methoxy-2-oxoethyl)benzoic acid (12) (0.985 g, 91% yield) as a white solid.1H NMR (CDCl3, 400 MHz) δ 8.08 (d, 2H, J = 8.4Hz), 7.40 (d, 2H, J = 8.4Hz), 3.72 (s, 5H). The data obtained are in agreement with those reported in the literature WO2005/12220.

References

[1] Patent: WO2016/199111, 2016, A1. Location in patent: Paragraph 00146-00147
[2] Journal of Chemical Research - Part S, 1999, # 6, p. 378 - 379
[3] Patent: WO2005/12220, 2005, A2. Location in patent: Page/Page column 113
[4] Patent: WO2013/41407, 2013, A1. Location in patent: Page/Page column 34
[5] Patent: WO2014/125426, 2014, A1. Location in patent: Page/Page column 40