3-(3-METHOXYPHENYL)PROPIONIC ACID Chemical Properties

Melting point:

43-45 °C (lit.)

Boiling point:

318.1±17.0 °C(Predicted)

Density 

1.144±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in DMSO

pka

pK1:4.654 (25°C)

form 

Solid

color 

White to light yellow

Water Solubility 

Soluble in water.

BRN 

1874422

InChI

InChI=1S/C10H12O3/c1-13-9-4-2-3-8(7-9)5-6-10(11)12/h2-4,7H,5-6H2,1H3,(H,11,12)

InChIKey

BJJQJLOZWBZEGA-UHFFFAOYSA-N

SMILES

C1(CCC(O)=O)=CC=CC(OC)=C1

CAS DataBase Reference

10516-71-9(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29189900

MSDS

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

3-(3-METHOXYPHENYL)PROPIONIC ACID Usage And Synthesis

Chemical Properties

Brown, low melting solid

Uses

3-(3-Methoxyphenyl)propionic acid is used as pharmaceutical intermediates.

Definition

ChEBI: 3-Methoxybenzenepropanoic acid is a member of methoxybenzenes.

General Description

3-(3-Methoxyphenyl)propionic acid can be prepared by the catalytic (palladium on charcoal) reduction of its corresponding unsaturated acid with H₂.

Synthesis

3-Methoxycinnamic acid (8) (3.56 g, 19.98 mmol) was dissolved in methanol (100 mL) and 10% Pd/C catalyst (0.44 g) was added. The mixture was stirred in a hydrogen (balloon) atmosphere for 12 h at room temperature. Upon completion of the reaction, the reaction mixture was filtered through diatomaceous earth (Celite) and the diatomaceous earth was washed with ethyl acetate (3 x 30 mL). The filtrates were combined and the ethyl acetate and methanol were removed by evaporation under reduced pressure to give 3-(3-methoxyphenyl)propionic acid (10) (3.59 g, 19.7 mmol, quantitative yield). The product was characterized by 1H NMR (CDCl3, 600 MHz) and 13C NMR (CDCl3, 150 MHz) with the following data: 1H NMR δ 11.93 (1H, s), 7.27 (1H, t, J = 7.5 Hz), 6.88 (2H, m), 6.83 (1H, d, J = 8 Hz), 3.79 (3H, s), 3.79 (3H, s) 2.99 (2H, t, J = 7 Hz), 2.73 (2H, t, J = 7 Hz); 13C NMR δ 179.2, 159.9, 142.0, 129.6, 120.7, 114.2, 111.6, 54.9, 35.5, 30.6.

References

[1] MedChemComm, 2016, vol. 7, # 12, p. 2418 - 2427
[2] Patent: US2018/2355, 2018, A1. Location in patent: Paragraph 0094
[3] Journal of Organic Chemistry, 1992, vol. 57, # 4, p. 1262 - 1271
[4] Journal of Organic Chemistry, 1996, vol. 61, # 26, p. 9146 - 9155
[5] Tetrahedron Asymmetry, 2014, vol. 25, # 6-7, p. 578 - 582

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