ChemicalBook CAS DataBase List BENZYL GLYCIDYL ETHER

BENZYL GLYCIDYL ETHER synthesis

9synthesis methods

Product Name:BENZYL GLYCIDYL ETHER
CAS Number:2930-05-4
Molecular formula:C10H12O2
Molecular Weight:164.2

106-89-8 Synthesis

106-89-8
746 suppliers
$9.00/10 g

100-51-6 Synthesis

100-51-6
1389 suppliers
$5.00/100g

2930-05-4
114 suppliers
$8.00/5g

Yield:2930-05-4 94%

Reaction Conditions:

Stage #1:epichlorohydrin with tetrabutylammomium bromide;potassium hydroxide in water at 20;Cooling with ice;
Stage #2:benzyl alcohol in water at 10 - 20;

Steps:

7.1
A mixture of 50% w/w aqueous potassium hydroxide (30 mL), epichlorohydrin (157 mmol, 20 mL) and tetrabutylammonium bromide (2.35 mmol, 0.75 g) was vigorously stirred at room temperature and cooled in an ice bath. Benzyl alcohol (96.0 mmol, 10 ml) was added dropwise, while maintaining the reaction temperature at about 10° C. by cooling the reaction mixture in an ice bath. The reaction mixture was then allowed to stir at room temperature overnight after which it was poured onto ice/water, and the aqueous phase extracted with diethyl ether. The organic phases were combined and washed with brine to neutrality and dried (Na₂SO₄). The solution was concentrated under reduced pressure. The residue was purified by flash chromatography (silica, 2-10% ethyl acetate/heptane) to give 14.8 g (94%) of 2-benzyloxymethyl-oxirane. C₁₀H₁₂O₂ (164.21), LCMS (ESI): 165.10 (M+H). ¹H NMR (CDCl₃), 300 MHz), δ 7.26-7.38 (m, 5H), 4.59 (q, 2H), 3.77 (dd, 1H), 3.45 (dd, 1H), 3.19 (m, 1H), 2.80 (t, 1H), 2.63 (dd, 1H).

References:

SANOFI-AVENTIS US2010/75994, 2010, A1 Location in patent:Page/Page column 22-23

FullText