1-(2-Hydroxy-5-methylphenyl)ethanone Chemical Properties

Melting point:

45-48 °C(lit.)

Boiling point:

112-114°C 12mm

Density 

1.079

refractive index 

1.5369 (estimate)

FEMA 

4594 | 2-HYDROXY-5-METHYLACETOPHENONE

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO : 50 mg/mL (332.96 mM; Need ultrasonic)

form 

powder to crystal

pka

10.46±0.18(Predicted)

color 

Light orange to Yellow to Green

Odor

at 1.00 % in dipropylene glycol. sweet heavy floral herbal

Odor Type

floral

Water Solubility 

Insoluble in water.

JECFA Number

2045

BRN 

1364840

LogP

2.52

CAS DataBase Reference

1450-72-2(CAS DataBase Reference)

NIST Chemistry Reference

Ethanone, 1-(2-hydroxy-5-methylphenyl)-(1450-72-2)

EPA Substance Registry System

Ethanone, 1-(2-hydroxy-5-methylphenyl)- (1450-72-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29147000

MSDS

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1-(2-Hydroxy-5-methylphenyl)ethanone Usage And Synthesis

Chemical Properties

yellow crystalline powder

Uses

2'-Hydroxy-5'-methylacetophenone is used to produce 2-ethyl-4-methyl-phenol. It is used as an intermediate in organic synthesis.

Definition

ChEBI: 2'-Hydroxy-5'-methylacetophenone is an aromatic ketone.

Preparation

Obtained by treatment of methyl 4-hydroxy-6-methyl-coumarin-3-carboxylate with potassium hydroxide at 200° (82%).

Synthesis

The general procedure for the synthesis of 2-hydroxy-5-methylacetophenone from p-cresyl acetate was as follows: p-tolyl acetate (10 g, 0.067 mol) and aluminum chloride (10.7 g, 0.08 mol) were added to a 500-mL round-bottomed flask. The reaction mixture was heated in an oil bath at 140-150°C for 5-6 hours. The reaction process was monitored by thin layer chromatography (TLC) using ethyl acetate:hexane as the unfolding agent. After completion of the reaction, the reaction mixture was quenched with crushed ice and the resulting solid product was extracted with ethyl acetate (2 x 50 mL). The organic phase was washed with brine solution (2 x 15 mL) and dried with anhydrous sodium sulfate. Subsequently, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by aqueous ethanol recrystallization to afford the target compound 2-hydroxy-5-methylacetophenone in 92% yield with a melting point of 45-48°C.

References

[1] Journal of Organic Chemistry, 1981, vol. 46, p. 4971 - 4975
[2] Journal of Chemical Research, Miniprint, 2003, # 12, p. 1258 - 1270
[3] Journal of Chemical Research, Synopses, 1999, # 9, p. 574 - 575
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 7, p. 734 - 736
[5] Journal of Chemical Research, Miniprint, 1998, # 10, p. 2678 - 2695

1-(2-Hydroxy-5-methylphenyl)ethanone(1450-72-2)Related Product Information

• 1-(2-Hydroxy-5-methylphenyl)ethanone
• 5-HYDROXY-7,4'-DIMETHOXY-6,8-DIMETHYLFLAVONE
• 6,8-DIMETHYL-4',5,7-TRIHYDROXYFLAVANONE
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• SCIADOPITYSIN
• USNIC ACID
• ORIENTIN
• (+)-Usniacin
• HOMOORIENTIN
• 6-METHYL-4-CHROMANONE
• 2-HYDROXY-5-METHYLBENZOPHENONE
• 2'-HYDROXY-4',5'-DIMETHYLACETOPHENONE
• ROTTLERIN
• VITEXIN-4'-RHAMNOSIDE(RG)
• (-)-USNIC ACID
• Vitexin
• LUTEONE
• 2',4'-DIHYDROXY-3'-METHYLACETOPHENONE