4-(4-Methoxyphenyl)butyric acid Chemical Properties

Melting point:

56-59 °C (lit.)

Boiling point:

196 °C / 10mmHg

Density 

1.116±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Slightly soluble in methanol. Insoluble in chloroform.

form 

Powder

pka

4.76±0.10(Predicted)

color 

Cream to slightly yellow

Water Solubility 

994.9g/L(37 ºC)

BRN 

2416568

InChI

InChI=1S/C11H14O3/c1-14-10-7-5-9(6-8-10)3-2-4-11(12)13/h5-8H,2-4H2,1H3,(H,12,13)

InChIKey

LZHMNCJMXQKSBY-UHFFFAOYSA-N

SMILES

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

LogP

2.33

CAS DataBase Reference

4521-28-2(CAS DataBase Reference)

NIST Chemistry Reference

4-(4-Methoxyphenyl)butyric acid(4521-28-2)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29189900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

4-(4-Methoxyphenyl)butyric acid Usage And Synthesis

Chemical Properties

cream to slightly yellow powder

Uses

4-(4-Methoxyphenyl)butyric acid on demethylation with pyridinium hydrochloride affords 4-hydroxyphenylbutyric acid, a key starting material for the synthesis of preclinical candidate LY518674.

Synthesis

Step G: 4-(4-methoxyphenyl)-4-oxobutanoic acid (40 g) was suspended in a solvent mixture of acetic acid (100 ml) and tetrahydrofuran (THF, 100 ml). To this suspension, 10% palladium-carbon catalyst (50% wet weight, 4 g) was added, followed by stirring the reaction mixture under hydrogen atmosphere (0.4 MPa) for 9 hours. Upon completion of the reaction, it was filtered through a diatomaceous earth pad to remove the catalyst. Toluene was added to the filtrate and the solvent was subsequently removed by distillation under reduced pressure to afford 4-(4-methoxyphenyl)butanoic acid in quantitative yield. The product was characterized by 1H-NMR (CDCl3): δ 1.89 (m, 2H), 2.32 (t, J=7.3 Hz, 2H), 2.58 (t, J=7.4 Hz, 2H), 3.73 (s, 3H), 6.78-6.82 (m, 2H), 7.03-7.08 (m, 2H), 10.96 (brs, 1H).

References

[1] Patent: EP1726587, 2006, A1. Location in patent: Page/Page column 33
[2] Chemistry of Natural Compounds, 2003, vol. 39, # 4, p. 404 - 406
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1998, vol. 37, # 3, p. 281 - 284
[4] Research on Chemical Intermediates, 2017, vol. 43, # 10, p. 5933 - 5942
[5] Journal of Organic Chemistry, 1990, vol. 55, # 11, p. 3537 - 3543

4-(4-Methoxyphenyl)butyric acid(4521-28-2)Related Product Information

• 4-Methoxyphenylacetone
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• 4-Phenylbutyric acid
• p-Anisaldehyde
• 4-Methoxybenzylchloride
• (Trifluoromethoxy)benzene
• Butyric Acid
• MCPB
• Anisole
• 3-Methoxybenzaldehyde
• 4-(4-HYDROXYPHENYL)BUTANOIC ACID
• 8-Hydroxyquinoline-N-oxide
• 3-(4-METHOXYBENZOYL)PROPIONIC ACID
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• 4-(3,4-DIMETHOXYPHENYL)-4-OXOBUTYRIC ACID
• 3-(3-FLUORO-4-METHOXYBENZOYL)PROPIONIC ACID
• 3-(4-ETHOXYBENZOYL)PROPIONIC ACID
• ETHYL 3-(4-METHOXYBENZOYL)PROPIONATE