2549-42-0

Basic information

• Product Name: GAMMA-METHYL-EPSILON-CAPROLACTONE
• Synonyms: GAMMA-METHYL-EPSILON-CAPROLACTONE;2-Oxepanone, 5-Methyl-
• CAS NO: 2549-42-0
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• Mol File: 2549-42-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 103 °C(Press: 5 Torr)
• Appearance: /
• Density: 0.973±0.06 g/cm3(Predicted)
• CAS DataBase Reference: GAMMA-METHYL-EPSILON-CAPROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: GAMMA-METHYL-EPSILON-CAPROLACTONE(2549-42-0)
• EPA Substance Registry System: GAMMA-METHYL-EPSILON-CAPROLACTONE(2549-42-0)

Safety Data

• Hazardous Substances Data: 2549-42-0(Hazardous Substances Data)

Upstream product

• 15876-35-4 trans-1-Methoxy-4-methylcyclohexane 
• 25904-15-8 cis-1-Methoxy-4-methylcyclohexane 
• 589-92-4 1-methylcyclohexan-4-one 
• 91-01-0 1,1-Diphenylmethanol 

Downstream Products

• 4089-71-8 (R,S)-3-methyl-1,6-hexanediol 
• 26330-65-4 6-ethyl-3-methyloct-6-en-1-ol 
• 26330-63-2 6-ethyl-3-methyloctane-1,6-diol 
• 1561-11-1 4-methylhexanoic acid 
• 57093-76-2 Methyl cis-4-methylcyclohexaneacetate 
• 57093-75-1 Methyl trans-4-methylcyclohexaneacetate 

Relevant articles and documents

ε-Caprolactone manufacture via efficient coupling Baeyer-Villiger oxidation with aerobic oxidation of alcohols

To avoid the use of peracids oxidant or highly concentrated hydrogen peroxide which is potentially hazardous and explosive, herein, a new route to ε-caprolactone was developed in which molecule oxygen was employed as the terminal oxidant. The commercial available N-hydroxyphthalimide and ammonium cerium nitrate were used as the key catalysts for the increased yield of ε-caprolactone. For instance, the selectivity of ε-caprolactone was obtained 92 % with 85 % conversion of cyclohexanone which was comparable to the strategies using highly concentrated hydrogen peroxide. The sacrificed alcohols were transformed into corresponding ketones which were also valuable chemicals. Furthermore, the efficiency of the alcohols was achieved to unprecedented 52 %. The Baeyer-Villiger oxidation of various other cycloalkanones was also examined. The substituent group effect on the efficiency of sacrificed alcohols was investigated in which weak electron-donating substituent induced nearly quantitative yield of ε-caprolactone. The reaction mechanism was studied with the help of electron paramagnetic resonance which indicated the existence of a radical pathway.

Oxidative Cleavage of Methyl Ethers Using the HOF*CH3CN Complex

HOF*CH3CN complex, made easily by bubbling fluorine diluted with nitrogen through aqueous acetonitrile, proved to be a suitable oxidizer for various methyl ethers.Secondary ethers are oxidized to ketones and even to lactones via Baeyer-Villiger type of oxidation.The reaction is ionic, and the reagent's electrophilic oxygen attacks the relatively electron rich C-H bond α to the ether moiety.It was found that the more sterically hindered is the C-H bond in question, the slower the reaction.In cases where this bond is an electron poor one as in benzoin methyl ether (9), no reaction takes place.When labeled H(18)OF*CH3CN is used on a (16)O methyl ether, the resulting ketone possesses only the heavier oxygen isotope.Primary methyl ethers are somewhat slower to react, but they too were oxidized in very good yields to acids via the corresponding aldehydes.