(2-HYDROXY-5-METHOXYPHENYL)(PHENYL)METHANONE synthesis

13synthesis methods

Product Name:(2-HYDROXY-5-METHOXYPHENYL)(PHENYL)METHANONE
CAS Number:14770-96-8
Molecular formula:C14H12O3
Molecular Weight:228.24

Preparation by Friedel–Crafts acylation of hydroquinone dimethyl ether with benzoyl chloride in the presence of aluminium chloride, in carbon disulfide first at 25° for 48 h, then at 50° for 30 min (55%) or at r.t. for 48 h (by-product).

Methanone, [5-methoxy-2-(2-pyridinyloxy)phenyl]phenyl-

1173294-88-6
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(2-HYDROXY-5-METHOXYPHENYL)(PHENYL)METHANONE

14770-96-8
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Yield:14770-96-8 88%

Reaction Conditions:

Stage #1: (5-methoxy-2-(pyridin-2-yloxy)phenyl)(phenyl)methanonewith methyl trifluoromethanesulfonate in toluene at 100; for 2 h;Inert atmosphere;
Stage #2: with sodium in methanol at 80; for 0.25 h;Inert atmosphere;

Steps:

1 4.4. Typical procedure for the removal of 2-pyridinyl directing group

General procedure: To a solution of phenyl(1-(pyridin-2-yloxy)naphthalen-2-yl)methanone (4f) (97.6 mg, 0.3 mmol) in toluene (10 mL) under N₂ was added MeOTf (60 μL, 0.52 mmol). The reaction mixture was stirred under N₂ at 100 °C for 2 h. The reaction mixture was allowed to cool to ambient temperature. The solvent was evaporated to obtain the residue, which was dissolved in dry methanol (5.0 mL) and was added to a solution of Na (165 mg, 7.2 mmol) in dry methanol (5.0 mL) under N₂. The reaction mixture was heated at 80 °C for 15 min. The reaction mixture was allowed to cool to ambient temperature and the solvent was evaporated in vacuo. Water was added, and the resulting mixture was extracted with EtOAc. The organic layer was dried over MgSO₄. After filtration and evaporation of the solvents in vacuo, the residue was purified by column chromatography on silica gel (n-hexanes/EtOAc=40:1-20:1) to yield 5a (66.3 mg) in 89% yield.

References:

Kim, Minyoung;Sharma, Satyasheel;Park, Jihye;Kim, Mirim;Choi, Yeonhee;Jeon, Yukyoung;Kwak, Jong Hwan;Kim, In Su [Tetrahedron,2013,vol. 69,# 32,p. 6552 - 6559]

98-88-4 Synthesis