p-Toluenesulfonic acid monohydrate → HCID 17821461, compound

HRID 1728971Notes

Reaction equation

HRID 1728971 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][C:8](=O)[CH2:9]2)([CH3:4])([CH3:3])[CH3:2].[CH3:15][Mg]Br.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:15][C:8]1[CH2:9][C:10]2[C:6]([CH:7]=1)=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:13]=[CH:12][CH:11]=2

Participants

4

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19016875HCID 19016875, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 17821461HCID 17821461, compoundYield 33%

Procedure

3.6 g (19 mmol) of indanone c3 were reacted with 3.0 equivalents of methylmagnesium bromide and the mixture was worked up, analogously to instructions I.3. The reaction time was 17 hours at room temperature and a further 4 hours under reflux. The mixture was then refluxed with p-toluenesulfonic acid hydrate for 25 minutes. Chromatography gave 1.2 g (33%) of indene c4 as a yellow oil. Unused starting material could be recovered with hexane/ethyl acetate (9:1).

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-45abd94999224e9eafdf628face952a3
Source dataset
uspto-grants-1994_07
Patent number
US05329033

Reaction notes

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