Dimethyl Carbonate → 1H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-1-oxo-, methyl ester

HRID 1282400Notes

Reaction equation

HRID 1282400 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[C:12](=O)([O:15]C)[O:13][CH3:14]>[H-].[Na+].C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([C:12]([O:13][CH3:14])=[O:15])[CH2:5]2

Participants

5

Reactant 2

HCID 12021Dimethyl CarbonateHCID 1425995-Chloro-1-indanone

Product 1

HCID 110423911H-Indene-2-carboxylic acid, 5-chloro-2,3-dihydro-1-oxo-, methyl esterYield 48%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 24758Sodium hydrideSolvent

Procedure

It is furthermore known from J. Pharm. Sci. 67(1) 1978, 81, to prepare the chloro-substituted indanonecarboxylic acid ester 5-chloro-2-methoxycarbonyl-1-indanone starting from 3-chlorobenzaldehyde. Here, 3-chlorobenzaldehyde is initially reacted in pyridine with malonic acid to give 3-chlorocinnamic acid. Following hydrogenation of the ethylenic double bond and cyclization to the 5-chloro-1-indanone, the latter is then reacted with dimethyl carbonate in the presence of sodium hydride and benzene as solvent to give 5-chloro-2-methoxycarbonyl-1-indanone. This synthesis method has the disadvantage of the multistep mechanism which considerably increases the likelihood of the formation of various by-products, which is reflected in only a low yield of 48%. Additionally, the total reaction requires the repeated use of substances such as sodium hydride and benzene, which are expensive, problematic with respect to safety or hazardous to health.

Sources & evidence

ORD record
ord-505b1907c99f47eca769904e7043aa0e
Source dataset
uspto-grants-2002_09
Patent number
US06455725B1

Reaction notes

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