ChemicalBook CAS DataBase List 3,4-Dichloro-4'-hydroxybenzophenone

3,4-Dichloro-4'-hydroxybenzophenone synthesis

4synthesis methods

Product Name:3,4-Dichloro-4'-hydroxybenzophenone
CAS Number:60013-02-7
Molecular formula:C13H8Cl2O2
Molecular Weight:267.11

Preparation by reaction of 3,4-dichlorobenzoyl chloride,
? with phenol in the presence of aluminium chloride;
? with phenetole in the presence of aluminium chloride in carbon disulfide at r.t. overnight (40%);
? with anisole in the presence of aluminium chloride at 70° for 4 h, followed by demethylation of the obtained ketone with 48% hydrobromic acid in refluxing acetic acid for 47 h.

Methanone, (3,4-dichlorophenyl)(4-methoxyphenyl)-

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60013-02-7
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Yield:60013-02-7 77%

Reaction Conditions:

with boron tribromide in dichloromethane;

Steps:

121 Example 121

Example 121 (Reference Example) 3,4-Dichlorophenyl 4-hydroxyphenyl ketone 3,4-Dichlorophenyl 4-methoxyphenyl ketone (235 mg) obtained in Example 120 was dissolved in dichloromethane (2 ml), a solution of 1.0 M boron tribromide in dichloromethane (7 ml) was added while cooled in ice, and the admixture was stirred at room temperature for two days. The reaction mixture was then poured into ice water and partitioned between water and chloroform. The chloroform layer was dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by column chromatography on silica gel eluding with hexane/ethyl acetate to obtain 173 mg of the title compound (yield: 77%). ¹ H-NMR (DMSO-d₆, 500 MHz): δ 6.91 (d, J=8.5 Hz, 2H), 7.62 (dd, J=1.8, 8.6 Hz, 1H), 7.68 (d, J=8.5 Hz, 2H), 7.80 (d, J=7.9 Hz, 1H), 7.85 (d, J=1.8 Hz, 1H), 10.55 (s, 1H) Mass spectrometry data (FD-MS, m/z): 266 (M⁺), 268 (M⁺ +2)

References:

US6143764,2000,A

3024-72-4 Synthesis