Noe, Marco; Perosa, Alvise; Selva, Maurizio published an article in 2013, the title of the article was A flexible Pinner preparation of ortho esters: the model case of trimethyl orthobenzoate.Quality Control of (Trimethoxymethyl)benzene And the article contains the following content:
In the absence of addnl. solvents, a novel procedure was implemented for the synthesis of tri-Me orthoesters through the Pinner reaction. At 5 °C, the reaction of both aliphatic and aromatic nitriles (RCN; R = Et, Bu, Ph) with a moderate excess of MeOH and gaseous HCl gave the corresponding imidate hydrochlorides [RC(:NH)OR’·HCl] in excellent yields (>90%). At 25-65 °C, the methanolysis of alkyl imidate salts provided tri-Me ortho-propionate and valerate, while only traces of tri-Me orthobenzoate (TMOB) were observed However, the aromatic hydrochloride could be readily converted into the hydrogen phosphate salt [PhC(:NH)OR’·H3PO4] which, in turn, underwent a selective (>80%) reaction with MeOH to produce TMOB in a 62% isolated yield. This allowed for an unprecedented Pinner-type synthesis of TMOB starting from benzonitrile, rather than from the highly toxic trichloromethylbenzene. Overall, remarkable improvements in safety and process intensification were achieved. The experimental process involved the reaction of (Trimethoxymethyl)benzene(cas: 707-07-3).Quality Control of (Trimethoxymethyl)benzene
The Article related to flexible pinner preparation ortho ester trimethyl orthobenzoate safety, Physical Organic Chemistry: Addition, Elimination, and Substitution Reactions and other aspects.Quality Control of (Trimethoxymethyl)benzene
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics