494 Mr. H. D. Dakin. [May 29, 
Experimental. 
Chloracetylcatechol is prepared according to Dziergowski’s (10) directions 
by heating catechol (1 mol.) and chloracetic acid (1 mol.) with phosphorus 
oxychloride equal in weight to the chloracetic acid used. As the reaction in 
my hands has always followed a course which differs slightly from that 
described by Dziergowski, the following particulars are given. The mixture 
should be placed in a large dry flask—at least 1000 cc. capacity for 
50 grammes catechol—and carefully heated in the water-bath. The mixture 
rapidly becomes fluid and clear, changing after a time to a deep purple colour. 
The reaction must be carefully watched, as at a certain point a violent 
evolution of hydrochloric acid with much frothing is liable to occur, which 
makes it necessary to cool the flask temporarily. Heating is continued until 
the evolution of hydrochloric acid slackens, and the thick dark-coloured semi- 
solid mass is dissolved in about three volumes of hot water. The solution is 
filtered to remove a trace of oily impurity and then allowed to cool. The 
chloracetylcatechol crystallises out in very well defined crystals, which are 
usually somewhat discoloured but are easily purified by a single re-crystallisa- 
tion from boiling water. The yield is about equal in weight to the catechol 
taken. The dry substance must be handled with care, as although it is 
without smell, even minute traces of its dust have a very powerful irritant 
effect on the eyes and nose. 
Methylamino-acetylcatechol.—The first product of the action of methylamine 
upon chloracetylcatechol is a yellow crystalline methylamine salt 
(CH3.NH3.0.CgH3(OH).CO.CH2C1) (10), but this substance on prolonged 
digestion with excess of methylamine gives methylamino-acetylcatechol, as 
has also been shown by Stolz(8). For example, 10 grammes of chloracetyl- 
catechol is placed in a stoppered bottle and 25 c.c. of aqueous 33 per cent. 
methylamine added in portions of 5 c.c. each. The mixture is cooled between 
the successive additions. The ketone is almost immediately changed into the 
yellow crystalline salt, and after thorough shaking and allowing to stand for 
one or preferably two days, the mixture becomes dark brown from the 
separation of the crude base. The solid is filtered off and washed well with 
water, alcohol and ether, then shaken with a slight excess of dilute hydrochloric 
acid. The solution is filtered from any trace of unchanged chloroketone, 
concentrated and crystallised. Crystallisation is also economically effected 
by adding alcohol and subsequently ether to the concentrated aqueous 
solution, the hydrochloride being precipitated in the form of colourless 
crystals. The free base may be readily obtained from the hydrochloride by 
precipitating with ammonia and is, when pure, a colourless crystalline 
