2-Methylindanone → 1H-Indene, 2-methyl-

HRID 1004549Notes

Reaction equation

[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.[BH4-].[Na+]>>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

Reactant 2

HCID 2492622-Methylindanone

HCID 4311764Sodium borohydride

Product 1

HCID 165871H-Indene, 2-methyl-Yield 83.1%

Procedure

Analogously to Example D, 5.0 g (34 mmol) of 2-methyl-1-indanone (5) were reduced with 1.94 g (51 mmol) of NaBH4. The alcohol, which was not purified further, was then further reacted in the presence of 0.2 g of p-toluenesulfonic acid in 100 ml of toluene at 80° C. Chromatography on 100 g of silica gel (hexane/methylene chloride 9:1) gave 3.68 g (82%) of 2-methylindene (6).

Workup

customThe alcohol, which was not purified further
customwas then further reacted in the presence of 0.2 g of p-toluenesulfonic acid in 100 ml of toluene at 80° C

Sources & evidence

ORD record: ord-3dd6f0bc087644428955efc47b9b5283
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06051522

Reaction notes

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