Hydrogen Bromide → HCID 23666399, compound

A solution of sodium 3,4-dimethylphenoxide was prepared by adding slowly with stirring and under nitrogen a solution of 3,4-dimethylphenol (48.86, 0.4 mole) in 250 ml of tetrahydrofuran (distilled from lithium aluminum hydride) to a suspension of 50% sodium hydride (18.2 g, 0.4 mole) previously washed with hexane and in 250 ml of tetrahydrofuran. After stirring for 30 minutes at room temperature, all evolution of hydrogen ceased and 1-(2'-pyridyl)-2-bromoethanol* hydrobromide (28.3 g, 0.1 mole) was added all at once in solid form. The reaction mixture was refluxed under nitrogen overnight. The tetrahydrofuran was removed on the rotary evaporator, and the resulting oil was partitioned between water and methylene chloride. The methylene chloride layer was extracted with three 200 ml portions of 10% sodium hydroxide and dried over sodium sulfate. Removal of solvent gave a brown oil (23.82 g). This oil was dissolved in methanol and converted to the hydrochloride salt with ethereal hydrogen chloride. This salt was recrystallized from methanoldiethyl ether to give 16.20 g (57.9%) of an off-white crystalline solid, m.p. softens 161°-162° C., melts 163°-164° C. with decomposition.

1. additionby adding slowly
2. washpreviously washed with hexane and in 250 ml of tetrahydrofuran
3. temperatureThe reaction mixture was refluxed under nitrogen overnight
4. customThe tetrahydrofuran was removed on the rotary evaporator
5. customthe resulting oil was partitioned between water and methylene chloride
6. extractionThe methylene chloride layer was extracted with three 200 ml portions of 10% sodium hydroxide
7. dry with materialdried over sodium sulfate
8. customRemoval of solvent

ORD record

ord-837b10f4900b4b728e20ffe160be25c1

Source dataset

uspto-grants-1989_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04835164