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

HRID 912628Notes

Reaction equation

HRID 912628 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

3

Reactant 1

HCID 222283931-(4-T-Butylphenyl)-3-chloropropan-1-one

Product 1

HCID 110305765-Tert-butyl-2,3-dihydroinden-1-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

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

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

Sources & evidence

ORD record
ord-8443526f4dc04d4c99d10f6b41be2605
Source dataset
uspto-grants-2011_09
Patent number
US08026256B2

Reaction notes

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