Disclosed herein are processes for synthesizing 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5-yl)-pyridin-3-yl)methoxy)benzaldehyde (also referred to herein as Compound (I)) and intermediates used in such processes. Compound (I) binds to hemoglobin and increases its oxygen affinity and hence can be useful for the treatment of diseases such as sickle cell disease.

The present invention relates to a process for the preparation of elafibranor and novel synthesis intermediates.

The present disclosure relates, in general, to 5-halo-3,6-dichlorosalicylic acid compounds, 5-halo-3,6-dichlorosalicyaldehyde compounds, processes for preparing 5-halo-3,6-dichlorosalicylic acid compounds, processes for preparing 5-halo-3,6-dichlorosalicyaldehyde compounds, processes for preparing 3,6-dichlorosalicylic acid compounds, and processes that employ such compounds as intermediates in the preparation of the herbicide dicamba.

The present disclosure relates, in general, to 5-halo-3,6-dichlorosalicylic acid compounds, 5-halo-3,6-dichlorosalicyaldehyde compounds, processes for preparing 5-halo-3,6-dichlorosalicylic acid compounds, processes for preparing 5-halo-3,6-dichlorosalicyaldehyde compounds, processes for preparing 3,6-dichlorosalicylic acid compounds, and processes that employ such compounds as intermediates in the preparation of the herbicide dicamba.

The present disclosure relates, in general, to 5-halo-3,6-dichlorosalicylic acid compounds, 5-halo-3,6-dichlorosalicyaldehyde compounds, processes for preparing 5-halo-3,6-dichlorosalicylic acid compounds, processes for preparing 5-halo-3,6-dichlorosalicyaldehyde compounds, processes for preparing 3,6-dichlorosalicylic acid compounds, and processes that employ such compounds as intermediates in the preparation of the herbicide dicamba.

Disclosed herein are processes for synthesizing 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5-yl)-pyridin-3-yl)methoxy)benzaldehyde (also referred to herein as Compound (I)) and intermediates used in such processes. Compound (I) binds to hemoglobin and increases it oxygen affinity and hence can be useful for the treatment of diseases such as sickle cell disease.

The present disclosure relates, in general, to 5-halo-3,6-dichlorosalicylic acid compounds, 5-halo-3,6-dichlorosalicyaldehyde compounds, processes for preparing 5-halo-3,6-dichlorosalicylic acid compounds, processes for preparing 5-halo-3,6-dichlorosalicyaldehyde compounds, processes for preparing 3,6-dichlorosalicylic acid compounds, and processes that employ such compounds as intermediates in the preparation of the herbicide dicamba.

There is provided a method for producing hydroxypivalaldehyde (HPA), including steps (i) to (iii) below in this order, Step (i): a reaction step of reacting IBAL with FA to produce a reaction solution containing HPA, step (ii): an extraction step of extracting the reaction solution with an aldehyde solvent represented by formula (1) under basicity to obtain an extract containing HPA, and step (iii): a distillation and collection step of distilling the extract and then collecting HPA from the residue, ##STR00001## wherein R represents a saturated alkyl group having 3 or more and 7 or less carbon atoms, further wherein the distillation step of the step (iii) is a step of distilling an extract in the presence of water, and an amount of the water which is subjected to the distillation is 100 parts by mass or more and 2,000 parts by mass or less with respect to a total amount, 100 parts by mass, of isobutyraldehyde (IBAL) derived from a raw material and an aldehyde solvent represented by formula (1) in an extract which is subjected to the distillation. The method enables HPA to be mass-produced and the collecting ratio of HPA to be improved while selectively removing impurities other than water contained in HPA, specifically IBAL and the like. According to the method for producing HPA as mentioned above, it is possible to reduce the content of neopentyl glycol-isobutyrate, isobutylaldehyde-hydroxypivalaldehyde-acetal, and isobutylaldehyde-hydroxypivalaldehyde-aldol as specific impurities byproduced from HPA.

There is provided a method for producing hydroxypivalaldehyde (HPA), including steps (i) to (iii) below in this order, Step (i): a reaction step of reacting IBAL with FA to produce a reaction solution containing HPA, step (ii): an extraction step of extracting the reaction solution with an aldehyde solvent represented by formula (1) under basicity to obtain an extract containing HPA, and step (iii): a distillation and collection step of distilling the extract and then collecting HPA from the residue, ##STR00001## wherein R represents a saturated alkyl group having 3 or more and 7 or less carbon atoms, further wherein the distillation step of the step (iii) is a step of distilling an extract in the presence of water, and an amount of the water which is subjected to the distillation is 100 parts by mass or more and 2,000 parts by mass or less with respect to a total amount, 100 parts by mass, of isobutyraldehyde (IBAL) derived from a raw material and an aldehyde solvent represented by formula (1) in an extract which is subjected to the distillation. The method enables HPA to be mass-produced and the collecting ratio of HPA to be improved while selectively removing impurities other than water contained in HPA, specifically IBAL and the like. According to the method for producing HPA as mentioned above, it is possible to reduce the content of neopentyl glycol-isobutyrate, isobutylaldehyde-hydroxypivalaldehyde-acetal, and isobutylaldehyde-hydroxypivalaldehyde-aldol as specific impurities byproduced from HPA.

The presently disclosed and/or claimed inventive concept(s) relates generally to oxidative oxidized reaction products made from the mechanocatalytic oxidative depolymerization of lignin. More particularly, but without limitation, the mechanocatalytic oxidative depolymerization of lignin is performed in a non-aqueous/non-solvent based and solvent-free process, i.e., via a solid-solid mechanocatalytic oxidative reaction methodology. In one particular embodiment, the process of making such oxidative oxidized reaction products includes, without limitation, the step of mechanocatalytically reacting an oxidation catalyst with lignin or a lignin-containing material. The oxidative reaction products obtained from the process include, for example, at least one of vanillin, and syringealdehyde, vanillic acid, and syringic acid.