848362-81-2

Basic information

• Product Name: 2,3,6-trimethyl-5-[(all-rac,E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-4-[(tributylsilyl)oxy]phenyl acetate
• CAS NO: 848362-81-2
• Molecular Weight: 671.176
• Mol File: 848362-81-2.mol

Chemical Properties

• CAS DataBase Reference: 2,3,6-trimethyl-5-[(all-rac,E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-4-[(tributylsilyl)oxy]phenyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,6-trimethyl-5-[(all-rac,E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-4-[(tributylsilyl)oxy]phenyl acetate(848362-81-2)
• EPA Substance Registry System: 2,3,6-trimethyl-5-[(all-rac,E)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-4-[(tributylsilyl)oxy]phenyl acetate(848362-81-2)

Safety Data

• Hazardous Substances Data: 848362-81-2(Hazardous Substances Data)

Upstream product

• 848362-65-2 2,3,6-trimethyl-5-(3-methylbut-2-en-1-yl)-4-[(tributylsilyl)oxy]phenyl acetate 
• 2140-82-1 2,6,10,14-tetramethyl-1-pentadecene 
• 870-63-3 prenyl bromide 
• 556-82-1 3-methyl-2-buten-1-ol 
• 36592-62-8 4-acetoxy-2,3,5-trimethylphenol 
• 7541-49-3 3,7,11,15-tetramethyl-2-hexadecen-1-ol 
• 108-24-7 acetic anhydride 
• 995-45-9 tributylchlorosilane 
• 848362-63-0 4-hydroxy-2,3,6-trimethyl-5-(3-methylbut-2-en-1-yl)phenyl acetate 

Relevant articles and documents

A new route to vitamin E Key-intermediates by olefin cross-metathesis

Ru-Catalyzed olefin cross-metathesis (CM) has been successfully applied to the synthesis of several phytyl derivatives (2b, 2d-f, 3b) with a trisubstituted C=C bond, as useful intermediates for an alternative route to α-tocopheryl acetate (vitamin E acetate; 1b) (Scheme 1). Using the second-generation Grubbs catalyst RuCl2(C21H 26N2)(CHPh)PCy3, (Cy = cyclohexyl; 4a) and Hoveyda-Grubbs catalyst RuCl2(C21H26N 2){CH-C6H4(O-iPr)-2} (4b), the reactions were performed with various C-allyl (5a-f, 7a,b) and O-allyl (8a-d) derivatives of trimethylhydroquinone-1-acetate as substrates. 2,6,10,14-Tetramethylpentadec-1-ene (6a) and derivatives 6c-e of phytol (6b) as well as phytal (6f) were employed as olefin partners for the CM reactions (Schemes 2 and 5). The vitamin E precursors could be prepared in up to 83% isolated yield as (E/Z)-mixtures.

A NEW ROUTE TO α-TOCOPHEROL, α-TOCOPHERYL ALKANOATES AND PRECURSORS THEREOF

The present invention is concerned with a novel process for the manufacture of (E/Z)-4-alkanoyloxy-3,5,6-trimethyl-2-phytylphenyI esters and silyl ethers, precursors of α- tocopherol and α-tocopheryl alkanoates, by cross-metathesis reaction of 2-alkenyl-3,5,6-trimethylhydroquinone dialkanoates or 4-alkanoyloxy-2-alkenyl-3,5,6-trimethylphenyI silylethers with 2,6,10,14-tetramethylpentadecene or a phytol derivative, e.g. phytyl acetate, in the presence of a cross-metathesis catalyst. As the cross-metathesis catalyst especially ruthenium metal carbene complexes are suitable which possess (a) ruthenium metal center(s), have an electron count of 16 or 18 and are penta- or hexa- coordinated. A further object of the invention is a process for the manufacture of α-tocopherol and α-tocopheryl alkanoates comprising this reaction.