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

HRID 2223381Notes

Reaction equation

HRID 2223381 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-a40f701221d943589a69576bf02a5708
Source dataset
uspto-grants-2008_05
Patent number
US07375126B2

Reaction notes

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