Sodium Hydroxide → HCID 14519922, compound

Participants

Reaction Steps

A mixture of 13.6 g (70 mmol) potassium 2-chlorobenzoate, 14.3 g (84 mmol, 1.2 equiv.) sodium 2-allyl-4-methylphenoxide, 0.8 g (8 mmol) CuCl and 2.6 g (8 mmol) tris[2-(2-methoxyethoxy]amine (TDA-1) in 200 ml anisole was heated and stirred under reflux for 3 hours. The anisole was removed under vacuum and the residue was extracted with dilute aqueous ammonia. After filtration to remove insoluble inorganics the aqueous solution was washed twice with ethyl acetate to remove remaining traces of anisole and excess 2-allyl-4-methylphenol. Acidification with conc. hydrochloric acid then gave an oil which was extracted into ethyl acetate. The organic layer was dried (Na2SO4) and the ethyl acetate was removed to give 10.6 g (47% yield) of crude 2-(2-allyl-4-methylphenoxy)benzoic acid (XVIII; R1 =H; R3 =4'-CH3), as an oil. The oil was dissolved in 50 ml of a chloroform solution of polyphosphate ester (PPE) and heated on a waterbath with the solvent being allowed to boil off. After 30 min the residue was basified with dilute sodium hydroxide solution and the oil product was extracted into petroleum ether. After being dried (Na2SO4) the solvent was removed to give 6.5 g (66% yield) of 4-allyl-2-methylxanthenone (XIX: R1 =H; R3 =2-CH3 ; m.p. (methanol) 97°-98° C. Anal. (C17H14O2) C,H.

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