1-(4-T-Butylphenyl)-3-chloropropan-1-one → 5-Tert-butyl-2,3-dihydroinden-1-one

HRID 451587

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:15])[CH2:12][CH2:13]Cl)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>S(=O)(=O)(O)O>[C:1]([C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][CH:6]=1)[C:11](=[O:15])[CH2:12][CH2:13]2)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 95 °C

Procedure

1-(4-tert-Butylphenyl)-3-chloro-1-propanone (22.25 g, 99 mmol) was dissolved in concentrated sulfuric acid (100 ml) and heated on a water bath at 95° C. for 2.5 hours. The reaction mixture was cooled, poured onto ice, and extracted with diethyl ether. The combined organic extracts were washed with saturated aqueous sodium bicarbonate, dried with magnesium sulfate, and the filtrate was evaporated under reduced pressure to provide the title compound which was used without further purification in the next step.

Workup

temperatureThe reaction mixture was cooled
additionpoured onto ice
extractionextracted with diethyl ether
washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate
dry with materialdried with magnesium sulfate
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-04a17c82613e47bba8fff76f66057048
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487116B2

Linked notes

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