Anisole → Indene

HRID 1608886Notes

Reaction equation

HRID 1608886 reaction equation
[C:1]1([CH2:7][C:8](Cl)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1(OC)C=CC=CC=1.CCS.[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S.[Cl-].[Al+3].[Cl-].[Cl-]>[CH2:11]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH:7]=[CH:8]1

Participants

6

Reactant 3

HCID 7519AnisoleHCID 7679Phenylacetyl chlorideHCID 19417624HCID 19417624, compound

Product 1

HCID 7219Indene

Reagents, catalysts & solvents 2

HCID 6348Carbon DisulfideSolventHCID 6451240Aluminum(III) ChlorideSolvent

Procedure

Treatment of p-methoxydeoxybenzoic (32) (FIG. 4) with PCl5 in refluxing benzene provided p-methoxy-α'-chlorostilbene 33 (Nagano, 1955), which underwent Friedel-Crafts conditions with anisole to furnish the triarylethylene 34. The carbonyl group in deoxybenzoic 32 was converted to a gem-dichloride intermediate, using phosphorus pentachloride, and with the subsequent elimination of HCl, the vinyl chloride 33 was obtained. Compound 32 was prepared using Friedel-Crafts conditions involving phenylacetyl chloride and anisole in carbon disulfide and aluminum chloride (BUCK, J. S. and IDE, W. S. (1932), "The isomeric desoxybenzanisoins", Journal of the American Chemical Society, 54, 3012). Demethylation of 35 was accomplished with EtSH/AlCl3, and 36 was isolated by column chromatography. Drying of phenol 36 at a high temperature resulted in the formation of an indene, which was observed previously (MAGARIAN, R. A., MELTON, S. AND NATARELLI, G. (1972), "2-Chloro-1-phenylindene from 1,1-dichloro-trans-2,3-diphenylcyclopropane", Journal of Pharmaceutical Sciences, 61, 1216). Compound 36 was isolated as the diacetate (37) using column chromatography.

Workup

  1. custom36 was isolated by column chromatography
  2. dry with materialDrying of phenol 36 at a high temperature

Sources & evidence

ORD record
ord-56862231c88a488cb3a685b5b1b7a5a7
Source dataset
uspto-grants-1995_03
Patent number
US05397802

Reaction notes

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