Formylation process for aromatic aldehydes

Details Formylation process for aromatic aldehydes Formylation process for aromatic aldehydes

1993-04-20

1994-03-15

Lone, Werren B.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568425, 568426, C07C 47575

Patent

active

052947440

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.

REFERENCES:
patent: 4192949 (1980-03-01), Merger et al.
patent: 4515987 (1985-05-01), Boden et al.
W. E. Smith, Journal of Organic Chemistry, vol. 37, No. 24, p. 3972 (1972).

Affiliated with

Also associated with

Rating

Formylation process for aromatic aldehydes does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Formylation process for aromatic aldehydes, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Formylation process for aromatic aldehydes will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1537180