Compounds Derived from Hydroxyacetic Acids

Martin, Aromatic Hydroxyketones Preparation and Physical Properties, 

Preparation by demethylation of a-acetoxy-p-methoxyacetophenone (SM) with aluminium chloride in refluxing benzene for 3 h (80%). In the reaction, deacetylation takes place simultaneously. SM was obtained by treatment of a-chloro-p-methoxyacetophenone with potassium acetate in ethanol [5068]. Preparation by action of boron trifluoride etherate with p-hydroxyphenyl diazomethyl ketone (SMI) in nitromethane under nitrogen at 22° for 15 min (81%). SMI, preparation given, melted at 145-150° (d) [5069]. 

Preparation by adding excess of concentrated hydrochloric acid to a warm concentrated aqueous solution of the potassium salt and cooling the solution 

Preparation by treatment of the sodium salt with aqueous hydrochloric add 

Also obtained from p-acetoxybenzoylcarbinol (SM2) by heating with 4% ethanolic potassium hydroxide for 45 min on a water bath (20%). SM2 was prepared from p-acetoxyphenyl diazomethyl ketone (m.p. 109-110°) after treahnent in dioxane with 2 N sulfuric acid at r.t. for 20 min, then at 40° until no more nitrogen evolved [5073], 

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