ChemicalBook CAS DataBase List 1-(4-METHOXY-PHENYL)-2-P-TOLYL-ETHANE-1,2-DIONE

1-(4-METHOXY-PHENYL)-2-P-TOLYL-ETHANE-1,2-DIONE synthesis

10synthesis methods

Product Name:1-(4-METHOXY-PHENYL)-2-P-TOLYL-ETHANE-1,2-DIONE
CAS Number:33425-19-3
Molecular formula:C16H14O3
Molecular Weight:254.2806

622-97-9 Synthesis

622-97-9
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4-METHOXYBENZENEDIAZONIUM TETRAFLUOROBORATE

459-64-3
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1-(4-METHOXY-PHENYL)-2-P-TOLYL-ETHANE-1,2-DIONE

33425-19-3
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Yield:33425-19-3 94%

Reaction Conditions:

with selenium(IV) oxide;palladium diacetate in dimethyl sulfoxide at 130; for 36 h;chemoselective reaction;

Steps:

General procedure for synthesis of benzil derivatives

General procedure: In a clean and dry 20 mL Schlenk tube added 1.2 mmol of diazonium salt, 1 mmol of styrene, 0.5 mol% palladium acetate and 1 mmol selenium dioxide and 2 mL DMSO. Reaction mixture was heated at 130 °C and progress of the reaction was moniterd on TLC and GCMS. After completion of reaction the reaction mass is cooled to room temperature and reaction mass was filtered to remove reduced selenium metal. Then added 5 ml ethyl acetate to filtrate. The filtrate washed with brine 5 ml x 2 times and then with water 10 ml x 1. Organic layer was separated and dried over sodium sulphate. The crude product was purified by column chromatoghraphy (Silica 60-120 mesh) using ether / ethyl acetate (9:1) as eluent to give the pure product.

References:

Jadhav, Vilas G.;Sarode, Sachin A.;Nagarkar, Jayashree M. [Tetrahedron Letters,2017,vol. 58,# 19,p. 1834 - 1838] Location in patent:supporting information