Hydrochloric Acid → 1-Methyl-1H-indene-2-carboxylic acid

HRID 1589294Notes

Reaction equation

HRID 1589294 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH:11]([CH3:14])[CH:12]=O)[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.[C:16]([CH:19]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:20](=O)[CH3:21])([OH:18])=[O:17].S(=O)(=O)(O)O>[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:7](=[CH:8][CH:9]=1)[CH2:12][C:11]([CH3:14])=[CH:10]2.[CH3:21][CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:19]1[C:16]([OH:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 130938682-Benzyl-3-oxobutanoic acidHCID 20195157HCID 20195157, compound

Product 2

HCID 123987441-Methyl-1H-indene-2-carboxylic acidHCID 20195156HCID 20195156, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Similarly, 5-amino-2-methylindene was prepared from the reductive cyclization of 3-(m-nitrophenyl)-2-methylpropionaldehyde with zinc and hydrochloric acid at elevated temperatures. Miller W. v. and Kinkelin G. Ber. 1886, 19, 1249 and 1520; Miller, W. v. and Rohde, G. ibid 1889, 22, 1830-1843. The difunctional 3-carboxy-4-phenyl-2-butanone reacted with excess sulfuric acid to give an unspecified yield of 1-methyl-2-carboxyindene. Roser, W. Ber. 1887, 20, 1574-1576.

Sources & evidence

ORD record
ord-cd8cc3ba7b0e481795684d28bb4615de
Source dataset
uspto-grants-1986_02
Patent number
US04568782

Reaction notes

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