A methanolic solution of sodium methoxide [from sodium (0.2 gram) and dry
methanol (3 ml)] was added dropwise during 20 minutes to a boiling solution
of methyl α,α-diphenylglycollate (11 grams) and 2-ethylpropylaminoethanol (6
grams) in light petroleum (150 ml, BP 80°-100°C) and the methanol that
separated was removed by using a Dean and Starke apparatus. At the end of
5 hours no further separation of methanol occurred and the reaction mixture
after being washed with water (3 x 20 ml) was extracted with 1N hydrochloric
acid (3 x 30 ml).
The acid extracts (after washing with 50 ml ether) were made alkaline with
aqueous 5 N sodium hydroxide solution, the liberated base was extracted into
ether (4 x 50 ml) and the ether extracts were dried (MgSO4). Treatment of
the extracts with hydrogen chloride gave the hydrochloride (11 grams, 70%),
which was obtained as rectangular plates, MP 164° to 166°C, after several
crystallizations from butanone.
