Benzyl glycidyl ether

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Benzyl glycidyl ether



Chiral HPLC
Column: Chiralcel OD-H (0.46 x 25 cm)
Detection: UV (254 nm) (In a few cases 214 nm was used.)
Benzyl Glycidyl Ether Analysis
Eluent: 10% iPrOH:90% Hexanes
Flow rate: 1.0 mL/min
Retention times of the two enantiomers: 8.2 and 9.0 minutes
Typical percentages of the two enantiomers using catalyst synthesized using L-Tartaric acid: 98.7% (8.2 min RT), 1.3% (9.0 min RT)
Typical percentages of the two enantiomers using catalyst synthesized using D-Tartaric acid: 3.5% (8.2 min RT), 96.5% (9.0 min RT)
3-Benzyloxy-1,2-propanediol Analysis
Eluent: 15% iPrOH:85% Hexanes
Flow rate: 0.9 mL/min
Retention times of the two enantiomers: 11.1 and 13.1 minutes
Typical percentages of the two enantiomers using catalyst synthesized using L-Tartaric acid: 84.0% (11.1 min RT), 16.0% (13.1 min RT)
Typical percentages of the two enantiomers using catalyst synthesized using D-Tartaric acid: 2.7% (11.1 min RT), 97.3% (13.1 min RT)
Optical Rotation
Jacobsen reports that the R enantiomer of benzyl glycidyl ether is the major one remaining using the (R,R) catalyst. (This is the catalyst produced using the L-Tartaric acid.) For a sample with >99% ee he reports: []²⁶_D +10° (c 5.2, MeOH).
Jacobsen reports that the R enantiomer of the diol is the major one produced using the (R,R) catalyst. (This is the catalyst produced using the L-Tartaric acid.) For a sample with 95% ee he reports: []²³_D -1.4° (c 3.31, EtOH).





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