1-(4-Butylphenyl)-3-chloropropan-1-one → 5-n-Butylindan-1-one

HRID 19715Notes

Reaction equation

HRID 19715 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:15])[CH2:12][CH2:13]Cl)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]>S(=O)(=O)(O)O>[CH2:1]([C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][CH:6]=1)[C:11](=[O:15])[CH2:12][CH2:13]2)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 216365181-(4-Butylphenyl)-3-chloropropan-1-one

Product 1

HCID 149399645-n-Butylindan-1-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1-(4-n-butylphenyl)-3-chloropropan-1-one (17.88 g, 79.8 mmol) in concentrated sulphuric acid (69 ml) is heated at 90° C. for 4 hours. After cooling to ambient temperature, the reaction mixture is poured on to ice and extracted with toluene. The combined organic phases are washed with saturated NaHCO3, brine, dried (MgSO4) and evaporated to afford the title compound. NMR δH 0.85 (t J 7.3 3H), 1.28 (sextet J 7.3 2H), 1.56 (quintet J 7.3 2H), 2.6 (m 4H), 3.02 (t J 5 2H), 7.10 (d J 8.3 1H), 7.20 (s 11H), 7.60 (d J 8.3 2H)

Workup

  1. additionthe reaction mixture is poured on to ice
  2. extractionextracted with toluene
  3. washThe combined organic phases are washed with saturated NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-18da456839034051bc86ac3c860c08c1
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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