938-45-4

Basic information

• Product Name: 2'-HYDROXY-5'-METHYLPROPIOPHENONE 95
• Synonyms: 2'-HYDROXY-5'-METHYLPROPIOPHENONE 95;1-(2-hydroxy-5-methylphenyl)-1-propanon;1-(2-hydroxy-5-methylphenyl)-1-Propanone;1-Propanone, 1-(2-hydroxy-5-methylphenyl)-;2-Propanoyl-4-methylphenol
• CAS NO: 938-45-4
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20108
• EINECS: 213-342-2
• Product Categories: Building Blocks;C15 to C38;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 938-45-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 2°C(lit.)
• Boiling Point: 251.67°C (rough estimate)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.070 g/mL at 25 °C
• Refractive Index: n20/D 1.545
• CAS DataBase Reference: 2'-HYDROXY-5'-METHYLPROPIOPHENONE 95(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-HYDROXY-5'-METHYLPROPIOPHENONE 95(938-45-4)
• EPA Substance Registry System: 2'-HYDROXY-5'-METHYLPROPIOPHENONE 95(938-45-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 2
• Hazardous Substances Data: 938-45-4(Hazardous Substances Data)

Usage

Preparation

Preparation by acylation of p-cresol with propionic acid using various catalysts,in the presence of boron trifluoride for 2 h at 80° (87%) or 70° (80%)in the presence of zinc chloride (Nencki reaction) for 1 h at reflux (55%).

Upstream product

• 104-93-8 p-methylanizole 
• 79-03-8 propionyl chloride 
• 51317-84-1 2-chloro-1-(2-hydroxy-5-methyl-phenyl)-propan-1-one 
• 91-66-7 N,N-diethylaniline 
• 51451-26-4 1-(2-hydroxy-6-methylphenyl)-1-propanone 
• 106-44-5 p-cresol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 10080-44-1 (2-hydroxy-5-methyl)propiophenone oxime 
• 7446-70-0 aluminium trichloride 
• 7495-84-3 p-tolyl propionate 
• 5451-69-4 2-(isopropyl)-5-methylphenyl propionate 
• 137937-37-2 1-(2-methoxy-6-methylphenyl)-1-propanone 

Downstream Products

• 1071378-07-8 1-(2-ethoxy-5-methyl-phenyl)-propan-1-one 
• 108293-72-7 1-<5-methyl-2-(2-propenyloxy)phenyl>-1-propanone 
• 82620-73-3 1-(2-methoxy-5-methylphenyl)propan-1-one 
• 102018-70-2 (3-ethyl-5-methyl-benzofuran-2-yl)-(4-methoxy-phenyl)-ketone 
• 4074-46-8 2-propyl-4-methylphenol 
• 84942-35-8 2-amino-4-methyl-6-propylphenol-hydrochloride 
• 57646-01-2 3,6-dimethyl-4H-chromen-4-one 
• 392721-71-0 1-(2-acetoxy-5-methyl-phenyl)-propan-1-one 
• 103863-52-1 bis-(2-hydroxy-5-methyl-3-propionyl-phenyl)-sulfide 
• 57442-43-0 4-methyl-2-(1-phenylimino)propyl phenol 

Relevant articles and documents

A Baker-Venkataraman retro-Claisen cascade delivers a novel alkyl migration process for the synthesis of amides

A simple extension of the carbamoyl Baker-Venkataraman rearrangement has been developed. If residual water in the reaction is not strictly excluded a Baker-Venkataraman retro-Claisen cascade takes place, giving amide products, in which an alkyl group apparently migrates between two functionalities of the substrate.

Microwave-induced deactivation-free catalytic activity of BEA zeolite in acylation reactions

Solventless liquid-phase acylation of p-cresol with different aliphatic carboxylic acids like acetic, propionic, butyric, hexanoic, octanoic, and decanoic acids was investigated over BEA zeolite under conventional as well as microwave heating. An unanticipated huge difference in activity was observed between two modes of heating. Under conventional heating, conversion of all the acids was less than 20%, while under microwave heating, the conversion was in the range of 50-80%. Ester formed through O-acylation and ortho-hydroxyketone formed through Fries rearrangement of the ester were the only products. Conversion of carboxylic acid increased with chain length up to hexanoic acid and then it showed a decrease in the trend. With all the acids, O-acylation occurred rapidly followed by slow conversion to ortho-hydroxyketone. The ketone/ester ratio increased with catalyst amount, temperature, and reaction time. Used catalyst samples were characterized by TGA, XRD, and IR studies to understand lower activity and deactivation behavior under conventional heating. The results showed absence of coke precursor/coke on the catalyst used in microwave-irradiated reactions in contrast to catalyst used in conventionally heated ones. Higher yield in the case of microwave-assisted reactions is attributed to the prevention of coke precursor/coke on the active sites by microwaves.

A comparative study: One pot synthesis of some prochiral ketones using conventional and microwave assisted methods

Polyphosphoric acid (PPA) has been used to synthesize a number of prochiral aryl ketones as well as α,β-unsaturated diaryl ketones by conventional and microwave assisted methods in moderate to good yield. The microwave assisted method is advantageous due to increased yield and high purity of products within incredible short period of time.