7  4,024,193  8  EXAMPLE  3  EXAMPLE4  EXAMPLE  I  EXAMPLE  5  EXAMPLE  2  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  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.  A  solution  was  prepared  comprising:  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  chloride  triphenyl  phosphine  (RuCl$_{2}$ (Pq,$_{3}$ ) 3  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.  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.  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.  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  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.  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.  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).  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.  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.  0.22  ml of  triethylamine  to  take  up HCI  generated  during  the  reaction.  1.5  grams  of  ruthenium  chloride  triphenyl  phosphine,  I  50  ml of  degassed  benzene,  and  Preparation  of  ruthenium  hydridochloride  triphenyl  phosphine  (RuHCl(Pq,$_{3}$ )a 