102547-88-6

Basic information

• Product Name: 3-hydroxy-2-methyl-1-cyclohexanone
• Synonyms: 3-hydroxy-2-methyl-1-cyclohexanone
• CAS NO: 102547-88-6
• Molecular Weight: 128.171
• Mol File: 102547-88-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-hydroxy-2-methyl-1-cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-2-methyl-1-cyclohexanone(102547-88-6)
• EPA Substance Registry System: 3-hydroxy-2-methyl-1-cyclohexanone(102547-88-6)

Safety Data

• Hazardous Substances Data: 102547-88-6(Hazardous Substances Data)

Upstream product

• 930-68-7 cyclohexenone 
• 54972-06-4 3,3-ethylenedioxy-2-methylcyclohexanone 
• 15681-48-8 lithium dimethylcuprate 
• 58008-75-6 7-Oxa-bicyclo[4.1.0]heptan-2-one oxime 
• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 103990-02-9 1,1:3,3-bis(ethylenedioxy)-2-methylcylcohexane 

Downstream Products

• 20007-99-2 Wieland-Miescher ketone 

Relevant articles and documents

Conversion of cycloalk-2-enones into 2-methylcycloalkane-1,3-diones - Assessment of various Tamao-Fleming procedures and mechanistic insight into the use of the Me3SiMe2Si unit

Conjugate addition of Me3SiMe2SiLi to cycloalk-2-en-1-ones, ketalization, Tamao-Fleming oxidation (Bu4NF, then H2O2, KHCO3), TPAP oxidation and acid hydrolysis generates 2-methyl cycloalkane-1,3-diones. Ketalization is needed in order to prevent addition of Me3Si- to the carbonyl. The pentamethyldisilanyl group has advantages over other silicon units that are used in Tamao-Fleming procedures.

Meerwein-Ponndorf-Verley-Type Reduction of Dicarbonyl Compounds to Hydroxy Carbonyl Compounds and α,β-Unsaturated Carbonyl Compounds to Allylic Alcohols Catalyzed by Zirconocene and Hafnocene Complexes

Group IVA metallocene complexes such as bis(η5-cyclopentadienyl)zirconium dihydrides, Cp2ZrH2 (1), and hafnium dihydrides, Cp2HfH2 (8), catalyze the chemoselective reduction of polycarbonyl compounds to hydroxy carbonyl compounds.For instance, the reduction of keto aldehydes 3-ketobutanal (2g) and 2-phenyl-2-ketoethanal (2h) proceeded selectively at aldehyde group to provide the corresponding hydroxy ketones 3g and 3h in 91percent and 93percent yields, respectively.Under similar conditions, however, cyclohexanediones were easily aromatized to benzenediols.On the other hand, 1 and 8 also catalyze the selective 1,2-reduction of various types of α,β-unsaturated carbonyl compounds, giving the corresponding allylic alcohols in good to excellent yields.Thus, steroidal dicarbonyl compounds, having an enone framework in their molecules Δ4-androstene-3,17-dione (11a) and Δ4-progestene-3,20-dione (11b) were reduced by 1 to 17-hydroxy-Δ4-androsten-3-one (12a) and 20-hydroxy-Δ4-progest-3-one (12b), which are essential human hormones, in 80percent and 67percent yields, respectively.