3-(4-METHOXYPHENOXY)PROPANOIC ACID Chemical Properties

Melting point:

110.5 °C

Boiling point:

321.7±17.0 °C(Predicted)

Density 

1.188±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.14±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C10H12O4/c1-13-8-2-4-9(5-3-8)14-7-6-10(11)12/h2-5H,6-7H2,1H3,(H,11,12)

InChIKey

SGTCAUQLJIKBMM-UHFFFAOYSA-N

SMILES

C(O)(=O)CCOC1=CC=C(OC)C=C1

Safety Information

HazardClass 

IRRITANT

HS Code 

2918999090

3-(4-METHOXYPHENOXY)PROPANOIC ACID Usage And Synthesis

Synthesis

General procedure for the synthesis of 3-(4-methoxyphenoxy)propionic acid from 3-(4-methoxyphenoxy)propanenitrile: 945 g (5.34 mol, 1 equiv.) of a sample of 3-(4-methoxyphenoxy)propanenitrile was loaded into a 22 L round-bottomed flask fitted with an overhead stirrer, and 4 L of concentrated hydrochloric acid was added to the stirred solid under nitrogen protection. 2 L of water was added slowly and the reaction mixture was heated to 100 °C and kept for 3.5 h, at which point the completion of the reaction was confirmed by high performance liquid chromatography (HPLC) analysis. The reaction was cooled to 10 °C by adding ice to the reaction mixture. After drying, 920 g of crude 3-(4-methoxyphenoxy)propionic acid was obtained. The crude product was dissolved in 5 L of 6 wt% sodium carbonate aqueous solution (pH=9), 2 L of dichloromethane (DCM) was added to the reaction vessel, and after thorough stirring, the organic layer was separated and discarded with a dispensing funnel. The aqueous layer was refilled into a 22 L flask and the pH of the aqueous layer was carefully adjusted to 4.0 by slowly adding 6 M hydrochloric acid.The precipitated solid was filtered and dried in a vacuum oven to give 900 g of 3-(4-methoxyphenoxy)propionic acid as a white solid (yield: 86.04%).1H NMR (450 MHz, CDCl3): δ=2.78 (t, 2H; CH2COOH); 3.70 (s, 3H; OCH3); 4.18 (t, 2H; OCH2); 6.78 (m, 4H; Ar-H).13C NMR (112.5 MHz, CDCl3): δ=34.703 (CH2COOH); 55.925 (OCH3); 64.088 (OCH2); 114.855 (CH3OCCH); 115.984 (CH2OCCH); 152.723 (CH3OC); 154.302 (CH2OC); 177.386 (COOH).

References

[1] Patent: WO2010/39256, 2010, A1. Location in patent: Page/Page column 91
[2] Patent: JP2016/41761, 2016, A. Location in patent: Paragraph 0182; 0183
[3] Patent: US9481671, 2016, B2. Location in patent: Page/Page column 68-69
[4] Patent: WO2008/150486, 2008, A2. Location in patent: Page/Page column 91
[5] ChemMedChem, 2015, vol. 10, # 12, p. 2042 - 2062

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