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The substituted acetophenone can be quite readily converted to the corresponding substituted styrene derivatives which are useful as monomers in the prepa› ration of a variety of polymeric materials including both homopolymers and copolymers with other mono- mers. The o-fluoroacetophenone derivative has been reported as exhibiting choleretic activity (J. Organic Chemistry, Vol. 27, p. 2669-70, 1962). The alpha› hydroxyacetophenone derivative is useful as an antifog› ger and sensitizer for silver halide emulsions ( Chem. Abstracts, Vol. 73, 82505n). 

In order to describe the present invention so that it may be more clearly understood, the following exam› ples are set forth. These examples are set forth primar- ily for the purpose of illustration and any enumeration of detail contained therein should not be interpreted as a limitation on the concept of the present invention. 

In the examples, low pressure hydrogenations - i.e., those at pressures up to about 60 psi hydrogen, were performed by the pop bottle technique described in Shriver, Manipulation of Air Sensitive Compounds, McGraw Hill, 1969, pages 156-158. Hydrogenations at higher pressures were carried out in a 300 ml stainless steel autoclave equipped with a temperature controller and temperature and pressure recorders. Samples were removed periodically during the course of the reaction, acetylated and analyzed by gas-liquid chromatography. When given, the amount of desired product in the sam› ple is expressed in terms of percent by weight based upon the total weight of unreacted starting material and product in the sample. 

The half life period (t$_{112}$ ) refers to the time, in min› utes, required for one half of the substrate to react to form the hydrogenated derivative thereof. 

Preparation of ruthenium chloride triphenyl phosphine (RuCl$_{2}$ (Pq,$_{3}$ ) 3 

Into a 200 ml pop bottle - i.e., a cappable, glass, pressure bottle, there was added a solution of 0.4 gram of ruthenium trichloride trihydrate dissolved in 50 ml of methanol and 2.4 grams oftriphenyl phosphine. The bottle was evacuated and the reaction mixture stirred for 3 hours at 700 C. At the end of this time, the reac- • • 1 d h tion mixture was coo e to room temperature, t e brown crystals were removed by filtration and were washed with methanol. There resulted 1.5 grams of product identified as ruthenium chloride triphenyl phosphine. Analysis of the product indicated 9.3 per- cent phosphorus and 67.75 percent carbon. These compare favorably with the theoretical values of 9.7 percent phosphorus and 67.76 percent carbon. 

Preparation of ruthenium hydridochloride triphenyl phosphine (RuHCl(Pq,$_{3}$ )a 

A solution was prepared comprising: 

1.5 grams of ruthenium chloride triphenyl phosphine, 

I 50 ml of degassed benzene, and 

0.22 ml of triethylamine to take up HCI generated during the reaction. 

Hydrogen was bubbled through the solution for 15 hours at the end of which time the solution was filtered and the solvet evaporated until crstallization occurred. The crystals were filtered, washed with ether and dried. 

## EXAMPLE I 

## EXAMPLE 2 

Into a 200 ml pop bottle there were added: I gram of 1,3 dihydroxy acetone, 10 ml of N-methyl-pyrrolidone, 15 ml of methyl cellosolve, and 2 ml of water. 

The bottle was capped, evacuated to remove oxygen and a slight positive pressure of hydrogen introduced. The resulting solution was heated to 75° C. and, to the solution there was added 0.25 grams of ruthenium chloride triphenyl phosphine prepared as described in Example I, dissolved in 5 ml of N-methyl pyrrolidone. The hydrogen pressure was increased to 50 psi and the temperatures of the reaction mixture maintained at 75° C. Samples of the reaction mixture were removed peri› odically during the course of the reaction and analyzed by gas-liquid chromatography. At the end of 18 min- utes, ‰ of the dihydroxy acetone had reacted - i.e., t$_{112 }$ was equal to 18 minutes. 

Into a 200 ml pop bottle there were added: 1.4 grams of 1,3 dichloroacetone, IO ml of N-methyl-pyrrolidone, 15 ml of methyl cellosolve, and • 2 ml of water. 

The bottle was capped, evacuated to remove oxygen and a slight positive pressure of hydrogen introduced. The resulting solution was heated to 75° C. and, to the solution there was added 0.25 grams of ruthenium chloride triphenyl phosphine prepared as described in Example 1, dissolved in 5 ml of N-methyl pyrrolidone. The hydrogen pressure was increased to 50 psi and the temperature of the reaction mixture maintained at 75° C. Samples of the reaction mixture were removed peri- odically during the course of the reaction and analyzed by gas-liquid chromatography. At the end of 10 min- utes, ‰ of the dichloroacetone had reacted - i.e., t$_{112 }$ was equal to 10 minutes. 

Into a 17 ml pop tube there was added 0.15 gram of ruthenium chloride triphepyl phosphine. The tube was capped, evacuated to remove oxygen and 5 ml of di- th 1 ’d dd d A r h • • me Y acetami e w:15 a e • s ig t positive pressure of hydrogen was mtrod~ced ~n~ the _brown slurry ~med to a deep red solution w1thm 5 mmutes. ~t this time, o. 5 ml of ortho-chloroacetop_henone was mtro: duced. The hydroge~ pres~ure was mcr~ased to 30 psi and th e t?be pl_aced man 011 ba th at 10~ C:• Sample~ of the reaction mixture we_re removed penod1cally d?n~g course of the reaction and analyzed by gas-hqu1d chromatography. After 3‰ hours, a sample contained 38 percent of the alcohol derivative. A second sample removed after 5 hours contained 52 percent by weight of I -( 2-chlorophenyl )ethanol 

## EXAMPLE 3 

## EXAMPLE4 

## EXAMPLE 5 

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