2-Mercaptoethanol → Ethanol, 2-[[(4-ethenylphenyl)methyl]thio]-

To a solution of potassium hydroxide (86 g, 1.3 moles) and 2,6-di-tert-butyl-p-cresol (1 g) in ethanol (1 liter) at room temperature was added under nitrogen atmosphere 2-mercaptoethanol (100 g, 1.3 moles), over fifteen minutes. Following addition the solution was stirred an additional hour at room temperature and then p-vinylbenzyl chloride (198 g, 1.3 moles) was added at room temperature over one hour. After addition, the mixture was allowed to reach ambient temperature overnight. The mixture was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter) and the solvent was washed with water (3×200 ml), then with saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed on a rotary evaporator. To the residue was added diethyl ether (200 ml) and petroleum ether (800 ml). The product crystallized and was then filtered to give a white solid: m.p. of 44°-45.5° C. Yield of 85%. Analysis calculated for C11H14OS: C. 68.0, H, 7.26, S, 16.50. Found: C, 67.7, H, 6.98, S, 15.37.

1. waitover fifteen minutes
2. additionaddition the solution
3. additionAfter addition
4. filtrationThe mixture was filtered
5. customthe solvent removed on a rotary evaporator
6. additionTo the residue was added dichloromethane (1.2 liter)
7. washthe solvent was washed with water (3×200 ml)
8. dry with materialwith saturated NaCl solution (200 ml), dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. customthe solvent removed on a rotary evaporator
11. additionTo the residue was added diethyl ether (200 ml) and petroleum ether (800 ml)
12. customThe product crystallized
13. filtrationwas then filtered
14. customto give a white solid

ORD record

ord-a6799965982b4b4484729b3c3149fb1c

Source dataset

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05210289