Ethyl Acetate → 5-(3-Phenoxypropoxy)indan-1,3-dione

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A solution of dimethyl 4-(3-phenoxypropoxy)phthalate (13.6 g., 0.0395 mole) in ethyl acetate (12 ml) was added to a 50% dispersion of sodium hydride in mineral oil (2.54 g) and the mixture heated at reflux for 4 hrs. After cooling, the mixture was triturated with 50% ethanol, ether and the yellow solid filtered off and added to a hot (70°-80° C.) 10% solution of hydrochloric acid (150 ml). After 2 mins a yellow oily solid separated which was isolated by decantation and taken up in acetone from which it crystallised on concentration to give 2.533 g (22%) of material of m.p. 91°-94° C., νmax (mull) 1740, 1710, 1605 cm-1 ; τ(DMSO) 7.78 (2H quintet; J 6.4 Hz); 6.68 (2H, s); 5.83 (2H, t, J 6.4 Hz); 5.62 (2H, t, J 6.4 Hz); 3.21- 2.44 (7H, m); 2.12 (1H, m). (Found; C, 72.97; H, 5.61; C18H16O4 requires; C, 72.96; H, 5.44%).

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