Adobiol,Yoshitomi,Japan,1974
The preparation of a similar compound in which a methoxyethoxy group
replaces the tetrahydrofurfuryloxy group in Bufetrol is described in the
following example. Nine grams of o-(2-methoxyethoxy)phenol is suspended in
50 milliliters of water containing 3.7 grams of potassium hydroxide, and 5.5
grams of epichlorhydrin is added thereto with stirring. The mixture is stirred
at room temperature for 7 hours, and then extracted with two 50 milliliter
portions of benzene. The extract is washed with water, dried over anhydrous
magnesium sulfate and the benzene is distilled off to give 8.5 grams of oily 1-
(2,3-epoxypropoxy)-2-(2-methoxyethoxy)benzene showing nD
20 = 1.5257.
This compound has the methoxyethoxy group in place of the 2-
tetrahydrofurfuryloxy group in Bufetrol.
To a solution of 1-(2,3-epoxypropoxy)-2-(2-tetrahydrofurfuryloxy)benzene in
methanol are added tert-butylamine and water, the mixture is allowed to
stand at 25°-30°C for 72 hours, and then the methanol is distilled off. The
residue is dissolved in toluene and the solution is extracted twice with 5%
oxalic acid. The aqueous extract is dried over potassium carbonate and
concentrated to give Bufetrol.
