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

Participants

Reaction Conditions

Reaction Steps

(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=300K, 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)).

Provenance & Evidence