C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 51/265 (2006.01) C07C 45/65 (2006.01) C07C 45/78 (2006.01) C07C 51/235 (2006.01)
Patent
CA 2190030
The object of the invention is a method for preparing 3-carboxy-4-hydroxybenzaldehydes and derivatives thereof from phenol compounds bearing formyl and/or hydroxymethyl groups in positions 2 and 4. Another object of the invention is the production of 4-hydroxybenzaldehydes from 3-carboxy-4-hydroxybenzaldehydes, and particularly the production of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde, known as "vanillin" and "ethyl vanillin" respectively. The method for preparing 3-carboxy-4-hydroxybenzaldehyde is characterised in that the group in position 2 of the phenol compound bearing formyl and/or hydroxymethyl groups in positions 2 and 4 is selectively oxidised to a carboxylic group, and optionally a hydroxymethyl group in position 4 to a formyl group. By thereafter decarboxylating the 3-carboxy-4-hydroxybenzaldehyde, a 4-hydroxybenzaldehyde is obtained.
La présente invention a pour objet un procédé de préparation de 3-carboxy-4- hydroxybenzaldéhydes et dérivés, à partir de composés phénoliques porteurs de groupes formyle et/ou hydroxyméthyle en position 2 et 4. Un autre objet de l'invention est la préparation de 4-hydroxybenzaldéhydes à partir de 3-carboxy-4-hydroxybenzaldehydes. L'invention concerne plus particulièrement la préparation du 3-méthoxy-4-hydroxybenzaldéhyde et du 3-éthoxy-4-hydroxybenzaldéhyde dénommés respectivement "vanilline" et "éthylvanilline". Le procédé de préparation d'un 3-carboxy-4-hydroxybenzaldéhyde est caractérisé par le fait l'on soumet un composé phénolique porteur de groupes formyle et/ou hydroxyméthyle en position 2 et 4 à une oxydation sélective du groupe en position 2 en groupe carboxylique, et éventuellement d'un groupe hydroxyméthyle en position 4 en groupe formyle. Une étape successive de décarboxylation d'un 3-carboxy-4 hydroxybenzaldéhyde conduit à un 4-hydroxybenzaldéhyde.
Rhone-Poulenc Chimie
Robic
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