2-Chloroethanol → 2-Chloroethyl 2-hydroxy-3-phenylpropionate

Participants

Reaction Steps

2-Chloroethyl 2-hydroxy-3-phenylpropionate was prepared from (S)-2-hydroxy-3-phenylpropionic acid and excess 2-chloroethanol essentially by the method described in Step 1 of Example 1; however, the distillate solidified after standing at 4° C.: b.p. 120° C./0.35 mm Hg; 1H NMR δ2.86 (bs, 1H), δ2.98 (dd, 1H, J=6.7 Hz and 14.0 Hz), δ3.13 (dd, 1H, J=4.6 Hz and 14.0 Hz), δ3.63 (t, 2H, J=5.6 Hz), δ4.35 (m, 2H), δ4.48 (dd, 1H, J=4.7 Hz and 6.6 Hz), δ7.2-7.3 (5H); 13C NMR 40.5, 41.0, 64.8, 71.3, 126.8, 128.3, 129.4, 136.2, 173.6 ppm; HRMS calcd for C10H9ClO3Tms (M-CH3) 285.0714, obsd 285.0756.

Provenance & Evidence