Hydrochloric Acid → 5-Acetyl-2,3-dihydro-1H-inden-2-yl acetate

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Reaction Conditions

Reaction Steps

To a mixture at 5-10° C. of aluminum chloride (AlCl3; 30.6 g, 0.229 mol) in carbon disulfide (CS2; 160 mL) was added acetyl chloride (12 mL, 13.2 g, 0.169 mol). To this mixture was added a solution of acetic acid indan-2-yl ester (19.9 g, 0.113 mol, prepared according to the method described in Can. J. Chem. 1967, 45, 1185) in acetyl chloride (12 mL) keeping the temperature below 11° C. The contents were stirred at 5° C. for 3 h and were then carefully added to ice-water (350 mL) containing concentrated HCl (60 mL). The mixture was extracted with CH2Cl2 (2×), and the combined extracts were washed with H2O and were dried over Na2SO4. Concentration gave the title compound (23.8 g, 97%) as a solid: 1H NMR δ 7.84 (s, 1H), 7.82 (m, 1H), 7.32 (d, J=7.0 Hz, 1H), 5.55 (m, 1H), 3.40-3.32 (m, 2H), 3.10-3.05 (m, 2H), 2.60 (s, 3H), 2.04 (s, 3H); EIMS m/z 158 ([M-AcOH]+, 42), 143 (100).

Provenance & Evidence