p-Toluenesulfonic acid monohydrate → HCID 17819667, compound

HRID 1197915Notes

Reaction equation

HRID 1197915 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=O)[CH2:8]2)([CH3:3])[CH3:2].[CH3:14][Mg]Br.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:14][C:7]1[CH2:8][C:9]2[C:5]([CH:6]=1)=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19016868HCID 19016868, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 17819667HCID 17819667, compoundYield 36%

Procedure

11.1 g (63.8 mmol) of indanone b3 were reacted with 2.5 equivalents of methylmagnesium bromide analogously to instructions I.3. The reaction time was 17 hours at room temperature. The mixture was then refluxed with p-toluenesulfonic acid hydrate for 25 minutes. Chromatography gave 3.9 g (36%) of indene b4 as a colorless oil.

Sources & evidence

ORD record
ord-bc0b276613514d25a0bced378ba0a2f9
Source dataset
uspto-grants-1994_01
Patent number
US05278264

Reaction notes

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