HCID 14442074, compound → (1-Oxo-2,3-dihydro-1H-inden-5-yl)acetic acid

HRID 1107031Notes

Reaction equation

HRID 1107031 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15]CC)=[O:14])=[CH:8][CH:7]=1)=[O:5]>S(=O)(=O)(O)O>[O:5]=[C:4]1[C:6]2[C:7](=[CH:8][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 14442074HCID 14442074, compound

Product 1

HCID 10241615(1-Oxo-2,3-dihydro-1H-inden-5-yl)acetic acidYield 58.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
20 °C

Procedure

(1-Oxoindan-5-yl)acetic acid can be obtained in the following way: a solution of 50.9 g of ethyl [4-(3-chloro-1-oxopropyl)phenyl]acetate in 950 ml of 95% sulphuric acid is heated for 1 hour at 100° C. The reaction mixture is cooled to a temperature in the region of 20° C. and then poured into 4 liters of ice-cold water. The mixture is extracted three times with 1.5 liter of dichloromethane. The organic phase is washed three times with 1 liter of water, then dried over magnesium sulphate and evaporated under reduced pressure. 22.2 g of (1-oxoindan-5-yl)acetic acid are thus obtained in the form of a cream solid melting at 141° C. (1H NMR spectrum in CDCl3, T=300 K, δ in ppm: 2.70 (2H, m, COCH2), 3.12 (2H, t, J=5 Hz, CH2), 3.68 (2H, s, CH2), 7.27 (1H, d, J=7 Hz, arom. CH), 7.45 (1H, s, arom. CH), 7.76 (1H, d, J=7 Hz, arom. CH)).

Workup

  1. extractionThe mixture is extracted three times with 1.5 liter of dichloromethane
  2. washThe organic phase is washed three times with 1 liter of water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4ff18750d25b4d1293f3a15f1b4aaaea
Source dataset
uspto-grants-2000_05
Patent number
US06057454

Reaction notes

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