75993-79-2

Basic information

• Product Name: methyl 5-phenyl-5-hydroxyhexanoate
• Synonyms: methyl 5-phenyl-5-hydroxyhexanoate
• CAS NO: 75993-79-2
• Molecular Weight: 222.284
• Mol File: 75993-79-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 5-phenyl-5-hydroxyhexanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-phenyl-5-hydroxyhexanoate(75993-79-2)
• EPA Substance Registry System: methyl 5-phenyl-5-hydroxyhexanoate(75993-79-2)

Safety Data

• Hazardous Substances Data: 75993-79-2(Hazardous Substances Data)

Upstream product

• 13984-50-4 methyl levulinate 
• 67-56-1 methanol 
• 98-86-2 acetophenone 
• 74900-27-9 1-(3-chloropropyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 
• 335645-38-0 2-(3-chloropropyl)-2-ethoxy-1,3-dioxolane 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 3128-06-1 5-ketohexanoic acid 
• 917-64-6 methyl magnesium iodide 
• 1501-04-8 Methyl 4-benzoylbutanoate 

Downstream Products

• 604807-76-3 methyl (E)-2-(1-hydroxy-1-methylethyl)-5-phenyl-4-hexenoate 

Relevant articles and documents

Masked ω-lithio ester enolates: Synthetic applications

The protocol of lithiation by means of lithium and a catalytic (5% molar) amount of DTBB (4,4'-di-tert-butylbiphenyl), applied to ω-chloro ortho ester 6 under Barbier-type conditions gives, after final acid-catalyzed methanolysis, the corresponding functionalized esters 8 or 9 (for chlorotrimethylsilane as electrophile) or, after ortho ester deprotection and acid catalyzed treatment, the δ-lactones 11. The procedure is also practical for bicyclic ortho esters 14: the β-chloro OBO ester derivate generates the γ-lactones 15 and the γ-chloro OBO ester gives corresponding esters 8.

Masked β-, γ- and δ-lithium ester enolates: Useful reagents in organic synthesis

The reaction of ω-chloro orthoesters 1 with lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5% molar) in the presence of different electrophiles [ButCHO, PhCHO, (CH2)5CO, Et2CO, PhCOMe, PhCH=NPh, Me3SiCl] in THF at -78°C leads, after hydrolysis and acid-catalysed methanolysis, to functionalised methyl esters 2. In the case of chlorotrimethylsilane, hydroxyethyl esters 2′ are isolated. The reaction is also applied to bicyclic orthoesters 3: whereas β-chloro derivatives and carbonyl compounds gives directly γ-lactones 4 after hydrolysis, the corresponding γ-chloro derivative affords the expected methyl esters after methanolysis.