4'-Hydroxyvalerophenone Chemical Properties

Melting point:

62-65 °C

Boiling point:

182-183 °C/3 mmHg(lit.)

Density 

1.0292 (rough estimate)

refractive index 

1.5390 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

8.13±0.15(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C11H14O2/c1-2-3-4-11(13)9-5-7-10(12)8-6-9/h5-8,12H,2-4H2,1H3

InChIKey

ZKCJJGOOPOIZTE-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2589-71-1(CAS DataBase Reference)

NIST Chemistry Reference

1-Pentanone, 1-(4-hydroxyphenyl)-(2589-71-1)

EPA Substance Registry System

1-Pentanone, 1-(4-hydroxyphenyl)- (2589-71-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-37/39-26

WGK Germany 

3

HS Code 

29182900

MSDS

• Language:English Provider:4-Pentanoylphenol
• Language:English Provider:ACROS

4'-Hydroxyvalerophenone Usage And Synthesis

Chemical Properties

white to light beige powder

Uses

4'-Hydroxyvalerophenone is an organic intermediate and pharmaceutical intermediate for the preparation of acylphenoxyacetic acid compounds.

Preparation

4'-Hydroxyvalerophenone is synthesized from phenol and valeryl chloride. It is a raw material intermediate for liquid crystals.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 6537, 1994 DOI: 10.1016/S0040-4039(00)78266-9

Synthesis

GENERAL METHOD: Phenol (0.28 mmol) was dissolved in trifluoromethanesulfonic acid (TfOH, 3 mL) with n-pentanoyl chloride (0.28 mmol) at 0 °C. The reaction mixture was gradually warmed up to room temperature according to the conditions shown in Table 2 and kept for an appropriate time. After completion of the reaction, the mixture was poured into a mixture of ice water and ethyl acetate. The organic layer was separated and washed sequentially with 1 M hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated. The crude product was purified by silica gel column chromatography to give 4-hydroxyvalerophenone. The spectral data of all the products were in agreement with those reported in the literature.

References

[1] Tetrahedron, 2011, vol. 67, # 3, p. 641 - 649
[2] Chemische Berichte, 1985, vol. 118, # 8, p. 3332 - 3349
[3] Tetrahedron, 1981, vol. 37, # 16, p. 2815 - 2821
[4] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 1998, vol. 54, # 2, p. 285 - 297
[5] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 6, p. 841 - 844

4'-Hydroxyvalerophenone(2589-71-1)Related Product Information

• Protocatechuic acid
• 2'-Hydroxyacetophenone
• 2-Hydroxyphenylacetic acid
• 4-Hydroxybenzoic acid
• 4-Methoxyphenol
• 4'-Hydroxyacetophenone
• Butylparaben
• 3-Hydroxybenzoic acid
• Methylparaben
• 4-Hydroxyphenylacetic acid
• 4-Hydroxybenzaldehyde
• 4-Hydroxy-D-(-)-2-phenylglycine
• 4'-Hydroxypropiophenone
• Methyl 4-hydroxyphenylacetate
• 4-Hydroxybenzyl alcohol
• (+)-Griseofulvin
• 5-METHOXY-1-INDANONE-3-ACETIC ACID
• 4'-Hydroxynonanophenone