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

HRID 391160Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]1[O:14][C:15](=[O:17])[CH3:16].Cl.[C:19](Cl)(=[O:21])[CH3:20]>C(=S)=S>[C:19]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[CH2:5][CH:6]([O:14][C:15](=[O:17])[CH3:16])[CH2:7]2)(=[O:21])[CH3:20]

Participants

Conditions

Temperature: 5 °C

Procedure

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).

Workup

customprepared
customthe temperature below 11° C
extractionThe mixture was extracted with CH2Cl2 (2×)
washthe combined extracts were washed with H2O
dry with materialwere dried over Na2SO4
concentrationConcentration

Sources & evidence

ORD record: ord-0776b0d30b1c4dd39b51a5e187bc0ee6
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383786B2

Reaction notes

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