ChemicalBook CAS DataBase List 3,5-Dichlorophenol

3,5-Dichlorophenol synthesis

11synthesis methods

Product Name:3,5-Dichlorophenol
CAS Number:591-35-5
Molecular formula:C6H4Cl2O
Molecular Weight:163

Catalytic hydrodechlorination of polychlorophenols in organic or aqueous media with a palladium catalyst was used to obtain 3-chlorophenol and 3,5-dichlorophenol.

Benzene, 1,3-dichloro-5-[2-(trimethylsilyl)ethoxy]-

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Yield:591-35-5 87%

Reaction Conditions:

Stage #1: [2-(3,5-dichlorophenoxy)ethyl]trimethylsilanewith cesium fluoride in N,N-dimethyl-formamide at 60; for 1 h;Inert atmosphere;
Stage #2: with water in N,N-dimethyl-formamide;Inert atmosphere;

Steps:

Procedure of trimethyl silane cleavage

General procedure: To a solution of [2-(phenoxy)-ethyl]-trimethyl-silane (Table-3, entry-1) (195mg, 1.0 mmol) in dry DMF (2 ml) was added cesium fluoride (576 mg, 3.0 mmol) and heated at 60°C for 1 h. Reaction mass was diluted with water and extracted with ethyl acetate (3 x 20 ml). The combined organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated under reduce pressure to give phenol 92mg (93% yield). Phenols of Table-3 are commercially available from Aldrich and its identity was confirmed by comparison of 1H NMR data with authentic sample.

References:

Dibakar, Mullick;Prakash, Anjanappa;Selvakumar, Kumaravel;Ruckmani, Kandasamy;Sivakumar, Manickam [Tetrahedron Letters,2011,vol. 52,# 41,p. 5338 - 5341] Location in patent:supporting information; experimental part

67492-50-6 Synthesis