16650-28-5

Basic information

• Product Name: 2-hydroxy-4-methyl-5-phenyloxolane
• Synonyms: 2-hydroxy-4-methyl-5-phenyloxolane
• CAS NO: 16650-28-5
• Molecular Weight: 178.231
• Mol File: 16650-28-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-hydroxy-4-methyl-5-phenyloxolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-4-methyl-5-phenyloxolane(16650-28-5)
• EPA Substance Registry System: 2-hydroxy-4-methyl-5-phenyloxolane(16650-28-5)

Safety Data

• Hazardous Substances Data: 16650-28-5(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 94100-73-9 (3S,4S,1'R,2'S,5'R,1Z)-4-hydroxy-1-(2-isopropyl-5-methylcyclohexyloxymethoxy)-3-methyl-4-phenylbut-1-ene 
• 84510-38-3 (3RS,4RS,1Z)-4-hydroxy-1-methoxymethoxy-3-methyl-4-phenyl-but-1-ene 
• 94100-69-3 tributyl(1-hydroxy-(E)-2-butenyl)stannane 
• 52884-17-0 2-methyl-1-phenyl-2,3-butadien-1-ol 

Downstream Products

• 16650-30-9 2-methyl-1-phenyl-butane-1,4-diol 
• 26704-17-6 trans-3-methyl-4-phenylbutan-4-olide 
• 26620-41-7 (RS,SR)-γ-hydroxy-β-methyl-γ-phenylbutanoic acid lactone 

Relevant articles and documents

Reactivity of α-(benzoyloxy)crotylstannane with aldehydes in liquid phase and on solid support. Synthesis of substituted lactones

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Substrate-directed diastereoselective hydroformylations, 1: Substrate-directed diastereoselective hydroformylation of methallylic alcohols - Development of an efficient catalyst-directing group for rhodium-catalyzed hydroformylation

The development of an efficient catalyst-directing group based on ortho-diphenylphosphanyl benzoate (o-DPPB) for the substrate-directed, diastereoselective hydroformylation of methallylic alcohols 5 is described. The hydroformylation of methallylic o-DPPB esters 9 provides the corresponding syn-aldehydes 10 with diastereoselectivities of up to 96:4. A specific steric demand of the substituent at the stereogenic center of the methallylic derivatives 9 was found to be necessary to achieve a high degree of stereoselectivity. Experiments have been performed that prove that the o-DPPB group acts as a catalyst-directing group by reversibly coordinating to the catalyst. The removal of the o-DPPB group was accomplished by means of alkaline hydrolysis, thereby furnishing the lactols 6. Oxidation of 6 provides the corresponding γ-lactones 7. VCH Verlagsgesellschaft mbH, 1997.

Synthesis of Optically Active (E)-1-Alkoxymethoxybut-2-enyl(tributyl)stannanes: Stereochemistry of their Thermal Reactions with Aldehydes

(1R)- and (1S)-1--(E)-but-2-enyl(tributyl)stannanes (8) and (9), whose configurations were assigned by correlation with (2R)- and (2S)-pentan-2-ol (14) and (15), react stereoselectively on heating with benzaldehyde to give (3S,4S)- and (3R,4R)-4-hydroxy-3-methyl-(Z)-1,2-enol ethers (16) and (18), respectively, the configurations of these products being established by correlation with pseudoephedrine.