Solketal synthesis

The new version of solketal synthesis based on the use of ethanol, can raise the yield to a practically quantitative, because ethanol is more effectively involved in the azeotropic removal of water and it also alters the chemical nature of the reaction medium by semiketal formation in interaction with acetone. It is known that the interaction of nonhindered lower alcohols and ketones gives almost quantitative formation of semiketals. This is detected by the change of physical parameters UV-absorbtion,... 

In the first step sodium hydride was used as a base in THF to introduce a benzyl protective group to the sn-3 position of the glycerol moiety by a Williamson ether synthesis using benzyl bromide. The benzylated solketal adduct was not isolated but introduced to deprotection of the isopropylidene... 

The most efficient method for the synthesis of racemic plasmenylcholines (52), an important class of glycerophospholipids, requires only six steps beginning from the inexpensive starting materials solketal or glycerol and acrolein. This method may also be applicable to the synthesis of chiral plasmenylcholines (Figure 13). ... 

Compound 128 has been synthesized by reaction of fluorescein methyl ester and 4-chloro-l-(4,4 -dimethoxytrityloxy)butane followed by detritylation and phosphitylation with bis-(N,N-diisopropylamino)methoxyphosphine. The phosphoramidite has been used for direct ligand incorporation at the 5 -end [319]. Synthesis of compound 129 proceeds from 5-carboxyfluorescein and isopropylidene glycerol (solketal). Incorporation at the 5 - or 3 -... 

Mesoporous MCM-type materials incorporating aluminum triflate were also considered for the synthesis of solketal, which is an acid-catalyzed reaction of acetone with glycerol, also known as ketalization reaction (Equation (8.50)) [119]. The selectivity to the desired product (solketal) was total, not being affected on varying the various reaction variables. On these catalysts the reaction does not produce other products such as hemiketal or six-membered cyclic ketal. 

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