3-Chloro-1-propanol → 4-(3-Hydroxy-propylsulfanyl)-phenol

4-Hydroxythiophenol (6.31 g, 50 mmol) was dissolved in ethanol (100 mL) and potassium tert-butoxide (6.72 g, 60 mmol) was added. The mixture was stirred until a clear, yellow solution was obtained. Then 3-chloro-1-propanol (4.20 ml, 50 mmol) was added with a syringe. The reaction mixture was stirred overnight at room temperature, the potassium chloride precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (150 mL) and the organic layer was extracted with water (2×100 mL) and brine (100 mL), dried over sodium sulphate and concentrated under reduced pressure. The resulting oil was dissolved in dichloromethane (50 mL) and hexane (100 mL) and left standing open overnight. The solid product was filtered off and dried under high vacuum. Yield: 5.34 g (58%) pale yellow solid.

1. customwas obtained
2. stirringThe reaction mixture was stirred overnight at room temperature
3. filtrationthe potassium chloride precipitate was filtered off
4. concentrationthe filtrate was concentrated under reduced pressure
5. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
6. extractionthe organic layer was extracted with water (2×100 mL) and brine (100 mL)
7. dry with materialdried over sodium sulphate
8. concentrationconcentrated under reduced pressure
9. dissolutionThe resulting oil was dissolved in dichloromethane (50 mL)
10. waithexane (100 mL) and left
11. filtrationThe solid product was filtered off
12. customdried under high vacuum

ORD record

ord-d43b190b97f046bf84d71a04af6c95f3

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745472B2