Trimethylolpropane → Trimethylolpropane monoallyl ether

참여 물질

반응 단계

1,1,1-Tris(hydroxymethyl)propane (trimethylolpropane) (13.20 g, 110 mmol) (Sigma-Aldrich) and 250 mL of THF were mixed in a 500-mL 3-neck round bottom flask with condensor. KOH (64.5 g 1.01 mol 3.0 equiv. per OH), and tetrabutyl ammonium bromide (TBAB) (0.345 g, 0.923 mol) (Sigma-Aldrich) were added via powder funnel, followed by addition of allyl bromide, (80.0 g, 0.923 mol, 3.0 equiv. per OH) via a 125-mL addition funnel over 10 mins. The reaction was then immediately placed into an oil bath at 70° C. for 24 hours. The reaction was monitored by TLC (110:1 hexanes:ethyl acetate), showing the product spot at Rf=0.4 and no spots for tri-, di-, or mono-allylsubstituted 1,1,1-Tris(hydroxymethyl)propane. The reaction mixture was vacuum-filtered through a 150-mL coarse glass-fritted Büchner funnel. The organic layer was diluted with diethyl ether (2×250 mL). The organic layer was washed with 5% K2CO3 (5×300 mL) and dried over MgSO4. Volatiles were removed by a rotary evaporator (40° C. bath temperature) to yield the trimethylolpropane allyl ether (TMPTAE), (11.95 g; 90% yield); and has the following spectra:

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