Benzene → 3,3-Dimethyl-1-indanone

HRID 1728990Notes

Reaction equation

HRID 1728990 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:7][C:8]([CH3:15])=[CH:9][C:10](OCC)=[O:11].F>>[CH3:7][C:8]1([CH3:15])[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[C:10](=[O:11])[CH2:9]1

Participants

4

Reactant 3

HCID 241BenzeneHCID 12516Ethyl 3,3-dimethylacrylateHCID 14917Hydrofluoric Acid

Product 1

HCID 3046283,3-Dimethyl-1-indanoneYield 96.7%

Conditions

Temperature
70 °C

Procedure

7.81 g (100 mmol) of benzene and 14.4 g (112 mmol) of ethyl 3,3-dimethylacrylate were reacted analogously with 100 g (5 mol) of liquid hydrogen fluoride and the mixture was stirred at 70° C. for 1 hour. The work-up was carried out analogously to Example A, giving 15.5 g of the compound (3) in a purity of 96% (GC). (Yield: 93.1% of theory). 1H-NMR spectra (100 MHz, CDCl3): 3:7.77-7.25 (m,4H), 2.57 (s,2H), 1.37 (s,6H).

Sources & evidence

ORD record
ord-f6dea1cbdf53459086647f1b3a15c660
Source dataset
uspto-grants-1994_07
Patent number
US05329049

Reaction notes

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