ChemicalBook CAS DataBase List Benzoic acid,2-(2,4-dimethylbenzoyl)-

Benzoic acid,2-(2,4-dimethylbenzoyl)- synthesis

5synthesis methods

Product Name:Benzoic acid,2-(2,4-dimethylbenzoyl)-
CAS Number:2346-63-6
Molecular formula:C16H14O3
Molecular Weight:254.28

85-44-9 Synthesis

85-44-9
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108-38-3
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2346-63-6
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Yield:2346-63-6 97%

Reaction Conditions:

Stage #1: phthalic anhydride;m-xylenewith aluminum (III) chloride at 55; for 5 h;cooling with salt-ice;
Stage #2: with hydrogenchloride in water;m-xylene;cooling with ice;

Steps:

216.A

Step A2-[(2,4-dimethylphenyl)carbonyl]benzoic acid. [00250] An ice/salt cold mixture of m-xylene (1 14 g, 1073 mmol) was treated with aluminium chloride (59.4 g, 446 mmol) (in three portions), followed by 2-benzofuran-1 ,3-dione (30 g, 203 mmol) (in three portions). The mixture was warmed to room temperature and stirred for 3 hours after which time the mixture turned to a thick white suspension. The mixture was heated to 55 °C for 2 hours, and cooled to room temperature. The thick mixture was slowly poured into ice cold 20% HCI and collected on filter paper. The filtered material was allowed to dry to give the desired product as a white solid (50 g, 97%). ¹H NMR (400 MHz,CHLOROFORM-d) δ ppm 7.98 - 8.07 (m, 1 H) 7.60 - 7.69 (m, 1 H) 7.51 - 7.59 (m, 1 H) 7.38 - 7.45 (m, 1 H) 7.01 - 7.13 (m, 2 H) 6.86 - 6.94 (m, 1 H) 2.61 (s, 3 H) 2.33 (s, 3 H); LC/MS (m/z) ES⁺ = 255 (M+1 ).

References:

WO2012/102985,2012,A1 Location in patent:Page/Page column 183-184