| Identification | More | [Name]
6,7-Dimethoxy-1-tetralone | [CAS]
13575-75-2 | [Synonyms]
6,7-DIMETHOXY-1-TETRALONE
6,7-DIMETHOXY-1-TETRALONE, 97%%
6,7-Dimethoxy-3,4-dihydro-2H-naphthalen-1-one | [Molecular Formula]
C12H14O3 | [MDL Number]
MFCD00134100 | [Molecular Weight]
206.24 | [MOL File]
13575-75-2.mol |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
|
| Hazard Information | Back Directory | [Uses]
6,7-Dimethoxy-1-tetralone was used in the synthesis of 2-bromotetralones by undergoing bromination. It was also used as a precursor to quinolines with dopaminergic activity, naphthols with anti-inflammatory activity and benzophenanthridine alkaloids with antitumor activity. | [Synthesis Reference(s)]
Tetrahedron Letters, 24, p. 2939, 1983 DOI: 10.1016/S0040-4039(00)88063-6 | [General Description]
6,7-Dimethoxy-1-tetralone reacts with 2-amino-4,5-dimethoxyacetophenone to form 5,6-dihydro-2,3,9,10-tetramethoxybenz[c]acridine. | [Synthesis]
General procedure for the synthesis of 6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one from 4-(3,4-dimethoxyphenyl)butyric acid: polyphosphoric acid (210 g) was added to a solution of dichloromethane (50 mL) in which 4-(3,4-dimethoxyphenyl)butyric acid (0.19 mol, 42 g) was dissolved, and the mixture was heated for 2 hr under reflux conditions. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was slowly poured into crushed ice. The pH of the solution was adjusted to 7-8 with alkali, and the precipitate precipitated was filtered and dried to give 6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one (36 g, 93.3% yield) as a white solid with a melting point of 94-96 °C (literature value: 96-98 °C).1H NMR (400 MHz, CDCl3): δ 7.51 (s, 1H), 6.67 (s 1H), 3.93 (s, 3H), 3.91 (s, 3H), 2.89 (t, J=6Hz, 2H), 2.60 (t, J=6.4Hz, 2H), 2.15-2.09 (m, 2H); 13C NMR (101MHz, CDCl3): δ197.10, 153.51, 147.96, 139.27 125.79, 110.22, 108.57, 55.98, 38.50, 29.44, 23.61. | [References]
[1] Synthetic Communications, 2009, vol. 39, # 15, p. 2664 - 2673
[2] Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4933 - 4938
[3] European Journal of Medicinal Chemistry, 2012, vol. 53, p. 52 - 63
[4] Pharmazie, 1981, vol. 36, # 2, p. 88 - 91
[5] Tetrahedron Letters, 2009, vol. 50, # 13, p. 1407 - 1410 |
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