4-Vinylbenzyl glycidyl ether synthesis

Yield:113538-80-0 86%

Reaction Conditions:

Stage #1: oxiranyl-methanolwith sodium hydride in N,N-dimethyl-formamide;mineral oil at 0;Inert atmosphere;
Stage #2: 4-Vinylbenzyl chloride in N,N-dimethyl-formamide;mineral oil at 20; for 4 h;Inert atmosphere;

Steps:

4-Vinylbenzyl glycidyl ether (S2)

General procedure: Under Ar atmosphere, sodium hydride (60% in mineral oil, 13.1 g, 327.60 mmol, 2.00 equiv) wassuspended in DMF (300 mL) and glycidol (27.15 mL, 459.1 mmol, 2.50 equiv) was added dropwise at 0oC. After the reaction mixture was stirred for 10~20 min, 1-(chloromethyl)-4-vinylbenzene (23.3 mL,163.80 mmol, 1.00 equiv) were added dropwise and the mixture was further stirred for 4 h at rt. Themixture was diluted with ethyl acetate (400 mL). Saturated aqueous NH4Cl (200 mL) was added to quenchthe reaction and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were driedover Na2SO4 and the solvent was removed in vacuo. The residue was purified by flash column chromatography to afford 4-vinylbenzyl glycidyl ether (S2) (27 g, 86%)

References:

Min, Hyemin;Miyamura, Hiroyuki;Kobayashi, Shu [Chemistry Letters,2016,vol. 45,# 7,p. 837 - 839] Location in patent:supporting information