3-(4-METHOXYPHENOXY)PROPANOIC ACID

3-(4-METHOXYPHENOXY)PROPANOIC ACID Property

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

HazardClass 

IRRITANT

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.

3-(4-METHOXYPHENOXY)PROPANOIC ACID Chemical Properties,Usage,Production

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