Formylation process for aromatic aldehydes
US5294744A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Apr 20, 1993 |
| Grant date | Mar 15, 1994 |
| Priority date | — |
| Expiry date | Apr 20, 2013 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C45/565
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A novel two-step reaction process for preparing 5-substituted-2-methoxybenzaldehyde compounds is disclosed wherein the substituent group is either isopropyl or trifluoromethoxy. The process involves (1) reacting a corresponding 4-substituted phenol compound with dimethyl carbonate in the presence of a tertiary-amine base to form the corresponding 4-substituted anisole compound, and (2) thereafter subjecting the latter intermediate product obtained in the first step to aromatic C-formylation on the ring with hexamethylenetetramine in the presence of trifluoroacetic acid, followed by hydrolysis, to ultimately yield the desired aldehyde compound. The two aromatic aldehyde compounds so obtained, viz., 2-methoxy-5-trifluoromethoxybenzaldehyde and 2-methoxy-5-isopropylbenzaldehyde, are known to be useful as intermediates that specifically lead to (2S,3S)-cis-3-(2-methoxy-5-trifluoromethoxybenzyl)amino-2-phenylpiperidine and (2S,3S)-cis-2-(diphenylmethyl)-N-[(2-methoxy-5-isopropylphenyl)methyl]-1-a zabicyclo[2.2.2]octane-3-amine, respectively. The latter final products, in turn, are both known to be useful in the field of medicinal chemistry as substance P receptor antagonists.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.