Hydrochloric Acid → 4-((2-Hydroxyethyl)thio)phenol

280 ml of 28% aqueous ammonia was added to a mixture of 50 g of 4-hydroxythiophenol and 54.56 g of ethylene bromohydrin and the mixture was stirred vigorously at room temperature for 2 h. 225 ml of concentrated hydrochloric acid was added thereto under cooling with ice to adjust the pH of the aqueous phase to 1. After extraction with ethyl acetate, the ethyl acetate layer was washed with a saturated aqueous common salt solution and then dried over anhydrous magnesium sulfate. The resulting solution was filtered and the filtrate was concentrated and subjected to silica gel column chromatography to obtain 44.77 g (yield: 66%) of the intended compound having the following physical properties:

1. temperatureunder cooling with ice
2. extractionAfter extraction with ethyl acetate
3. washthe ethyl acetate layer was washed with a saturated aqueous common salt solution
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationThe resulting solution was filtered
6. concentrationthe filtrate was concentrated

ORD record

ord-0c7c6dbc17004d2ab84c29e35709d84a

Source dataset

uspto-grants-1989_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04801603