138604-47-4

Basic information

• Product Name: Hexanal, 4-methyl-6-(phenylmethoxy)-, (S)-
• CAS NO: 138604-47-4
• Molecular Formula: C14H20O2
• Molecular Weight: 220.312
• Mol File: 138604-47-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Hexanal, 4-methyl-6-(phenylmethoxy)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Hexanal, 4-methyl-6-(phenylmethoxy)-, (S)-(138604-47-4)
• EPA Substance Registry System: Hexanal, 4-methyl-6-(phenylmethoxy)-, (S)-(138604-47-4)

Safety Data

• Hazardous Substances Data: 138604-47-4(Hazardous Substances Data)

Upstream product

• 96154-40-4 3,7-dimethyl-6-octenyl benzyl ether 
• 67245-14-1 (3S,6RS)-1-benzyloxy-6,7-epoxy-3,7-dimethyloctane 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 5949-05-3 (S)-Citronellal 
• 67245-13-0 benzyl ether of 6(R,S)-bromo-7-hydroxy-3(S),7-dimethyloctan-1-ol 
• 7540-51-4 (S)-3,7-dimethyl-6-octen-1-ol 
• 84237-05-8 (S)-((3,7-dimethyloct-6-enyloxy)methyl)benzene 
• 138524-36-4 benzyl ether of 3(S),7-dimethyloctane-1,6-(R,S)-7-triol 

Downstream Products

• 84184-37-2 (S)-3-Methylheptyl benzyl ether 
• 251968-34-0 (3S)-methyl-1-tosyloxyheptane 
• 1429470-03-0 (2S,4R)-1-(tert-butyldiphenylsilyloxy)-4-methylhept-6-en-2-ol 
• 1429470-19-8 C₁₁H₂₀O₂ 
• 1429470-17-6 C₁₇H₂₆O₃ 
• 1446944-50-8 (3S,11R,14RS)-1-benzyloxy-14,15-epoxy-3,11,15-trimethyl-7-hexadecyne 
• 1446944-78-0 (3S,11S,14RS)-1-benzyloxy-14,15-epoxy-3,11,15-trimethyl-7-hexadecyne 
• 1446944-49-5 (3S,11S)-1-benzyloxy-3,11,15-trimethyl-14-hexadecen-7-yne 
• 130797-63-6 (S)-3-Methylpentadecyl tosylate 
• 1446944-34-8 (S)-1-benzyloxy-3-methyl-7-pentadecyne 
• 1446944-33-7 (S)-6-benzyloxy-4-methylhexyl iodide 
• 1446944-90-6 (3S,11R)-3,11-dimethylpentadecyl tosylate 
• 1446944-54-2 (3S,11S)-3,11-dimethylpentadecyl tosylate 

Relevant articles and documents

Pheromone synthesis. Part 256: Synthesis of the four stereoisomers of 5,11-dimethylpentacosane, a new sex pheromone component of the male Galleria mellonella (L.), with high stereochemical purities as determined by the derivatization-HPLC analysis of the eight stereoisomers of 5,11-dimethyl-8-pentacosanol

Abstract All the four stereoisomers of 5,11-dimethylpentacosane (>96.8% purity) were synthesized via the stereoisomers of 5,11-dimethyl-8-pentacosanol, whose stereoisomeric compositions could be determined precisely by their low temperature HPLC analysis after derivatization. 5,11-Dimethyl-8-pentacosanol was prepared by a Grignard reaction between 3-methylheptylmagnesium bromide and 4-methyloctadecanal, both of which were prepared from the commercially available enantiomers of citronellal (97-98% ee). Alternatively, (R)-3-methyl-1-heptanol could be prepared from methyl (R)-3-hydroxybutanoate (100% ee). Pd/C-catalyzed hydrogenation of a 5-methyl-1-alkene caused partial racemaization at C-5.

Synthesis of all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2-octadecanone, sex pheromone components of the Lyclene dharma dharma moth, from the enantiomers of citronellal

The enantiomers of citronellal were converted to all the stereoisomers of 6-methyl-2-octadecanone, 14-methyl-2-octadecanone, and 6,14-dimethyl-2- octadecanone, the female-produced sex pheromone components of the Lyclene dharma dharma moth. Three wellestablished procedures, the Wittig reaction, alkylation of alkynes, and acetoacetic ester synthesis, were employed for the carbon-carbon bond formation to connect the building blocks.

A practical synthesis of 3(S)-methyl-heptanoic acid from (S)-citronellol

Chiral 3-methyl-heptanoic acid is readily accessible by functional group manipulation of optically active citronellol. In principle, this approach is general and could be applied to the synthesis of chiral 3-methyl-alkanoic acids seven carbon atoms in length and longer.