7-HYDROXY-4-METHOXY-INDAN-1-ONE synthesis
- Product Name:7-HYDROXY-4-METHOXY-INDAN-1-ONE
- CAS Number:98154-04-2
- Molecular formula:C10H10O3
- Molecular Weight:178.18
52428-09-8
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Yield:98154-04-2 24%
Reaction Conditions:
with cerium(III) chloride heptahydrate;sodium iodide in N,N-dimethyl-formamide; for 120 h;Reflux;Inert atmosphere;
Steps:
7-hydroxy-4-methoxyindan-1-one (7)
A mixture of 4,7-dimethoxyindan-1-one (5.0 g, 26.0 mmol, 1.0 eq), cerium chloride hepahydrate (29.1 g, 78.0 mmol, 3.0 eq) and sodium iodide (11.7 g, 78.0 mmol, 3.0 eq) in DMF (130 ml, 0.2 M, Bp 153 oC) was stirred under reflux for 5 days. The reaction mixture was cooled to room temperature and DMF was removed under reduced pressure at 70 oC water bath to leave dark-brown sticky oil material. The reaction mixture was diluted with H2O. The aqueous phase was extracted with CH2Cl2 (500 ml × 3) and washed with H2O. The combined organic layer was dried with MgSO4 and concentrated in vacuo. The residue was purified via flash column chromatography (EtOAc : Hexane = 1 : 2) to provide 7 (1.11 g, 24%, brsm 54%) as a orange powder. Rf : 0.67 (EtOAc : Hexane = 1 : 1) 1H NMR (CDCl3, 400 MHz) : d 8.55 (s, 1H), 7.01-6.99 (d, J = 8.0 Hz, 1H), 6.74-6.72 (d, J = 8.8 Hz, 1H), 3.84 (s, 3H), 3.05-3.03 (t, J = 4.8 Hz, 2H), 2.72-2.70 (t, J = 5.0 Hz, 2H) 13C NMR (CDCl3, 100 MHz) : d 210.3, 150.9, 149.8, 142.5, 123.6, 119.3, 114.0, 56.2, 36.1, 23.0 IR (neat, cm-1) : 3422, 2924, 2841, 1679, 1603, 1495, 1442, 1404, 1318, 1287, 1265, 1231, 1175, 1083, 1041, 992, 969, 945, 899, 836, 732, 715, 671 LR/MS (m/z) [M+H+] : 179.0
References:
Kim, Yun Yeong;Pyun, Yu Mi;Jeon, Bo Keun;Lee, Duck-Hyung [Bulletin of the Korean Chemical Society,2018,vol. 39,# 5,p. 597 - 598] Location in patent:supporting information
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