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Condensation products from propenal and pentaerythritol were first described in 1950. [4] [5] The synthesis is carried using a general synthesis method for acetals at acid pH (pH 3-5) by reacting an alcohol with an excess of aldehyde, which is stabilized with hydroquinone in the case of propenal, which tends to polymerize at elevated temperature.
The example below depicts the acetalisation reaction of D-ribose 1. With acetone or 2,2-dimethoxypropane as the acetalisation reagent the reaction is under thermodynamic reaction control and results in the pentose 2. The latter reagent in itself is an acetal and therefore the reaction is actually a cross-acetalisation.
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Used in a more general sense, the term X,Y-acetal also refers to any functional group that consists of a carbon bearing two heteroatoms X and Y. For example, N,O-acetal refers to compounds of type R 1 R 2 C(OR)(NR' 2) (R,R' ≠ H) also known as a hemiaminal ether or Aminal, a.k.a. aminoacetal.
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In organic chemistry, a hemiacetal is a functional group the general formula R 1 R 2 C(OH)OR, where R 1, R 2 is a hydrogen atom or an organic substituent. They generally result from the nucleophilic addition of an alcohol (a compound with at least one hydroxy group ) to an aldehyde ( R−CH=O ) or a ketone ( R 2 C=O ) under acidic conditions.
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