AlMar°ch'  Sh"*'  \    Ur  ethanes  of  Thymol  and  Carvacrol.  215 
of  82  per  cent.  It  was  crystallized  from  30  cc.  95  per  cent,  alcohol, 
but  caused  trouble  by  clogging  a  filter. 
The  thymol  compound  is  bright  yellow,  with  an  orange  tint 
which  deepens  on  exposure — it  is  somewhat  sensitive  in  this  respect 
— and  forms  thick  needles.  It  is  readily  soluble  in  heptane  and 
crystallizes  out  as  a  mush  of  pale  yellow  crystals.  The  solut'on  in 
alcohol  is  deep  orange,  almost  brown,  but  somewhat  lighter  in  hep- 
tane. The  alcoholic  solution  develops  an  odor  of  ethyl  benzoate, 
showing  that  alcoholysis  takes  place. 
Nitro so  carvacrol  dissolved  in  the  sodium  hydroxide  with  evolu- 
tion of  heat.  The  benzoyl  chloride  warmed  the  reaction  mixture 
and  an  oil  formed  which  solidified  slowly  and  as  a  film  of  brownish- 
yellow  color  on  the  walls.  It  was  washed  at  the  pump  and  dried.  It 
weighed  7.4  g.  It  melted  between  740  and  85°.  This  was  crystal- 
lized from  95  per  cent,  ethyl  alcohol,  in  which  it  is  more  readily 
soluble  than  the  thymol  derivative  and  crystallizes  well. 
M.  P. 
87° 
85° 
First  crop,  6.013  gm.  diluted  with  water. 
Second  crop,  -93  gm. 
Total,  6.94  gm. 
Yield,  98  per  cent. 
10.8  gm.  nitrosocarvarol  dissolved  in  the  equivalent  quantity  of 
2-N  potassium  hydroxide,  gave  16.39  g.  benzoyl  derivative  with  a 
yield  of  96  per  cent. 
This  compound  forms  rectangular  plates  with  bevelled  edges 
of  bright  yellow  color  with  orange  tint,  stable  in  the  air.  It  is  more 
soluble  than  the  thymol  compound.  The  alcoholic  solution  is  deep 
orange  to  brown  and  develops  an  odor  of  ethyl  benzoate.  The  solu- 
tion in  heptane  is  brownish  in  color  and  deposits  on  cooling  or  evapo- 
ration, yellow  prisms. 
The  characteristics  of  the  sodium  and  potassium  derivatives  of 
nitrosophenols  are  apparently  not  different  in  this  reaction,  because 
10  per  cent,  sodium  hydroxide  gave  yields  that  are  almost  quanti- 
tative and  the  same  for  2-N  potassium  hydroxide. 
Alkali  Carvacrol  Thymol 
NaOH  (2-N)  1 1  p.  c.  96  p.  o  89  p.  c. 
KOH  (2-N)  11  p.  c.  96  "  82  " 
