CONVERSION OF EPOXIDES INTO THIOCYANOHYDRINS
1381
EXPERIMENTAL
Products were characterized by comparison of their spectroscopic data ( H and 13C
NMR, IR) with those reported in the literature. All yields refer to isolated products. The
FT-IR spectra of neat samples between NaCl disks were obtained on a BOMEM 450
instrument. The high-field NMR spectra were obtained on a Bruker 400 MHz Avance
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ultrashield instrument. H and C chemical shifts are quoted relative to solvent resonance(s)
as internal standard.
Typical procedure for the solvent-free preparation of 2-hydroxy-3-phenoxy-
propyl thiocyanate from oxiranylmethyl phenyl ether using CMPI/NH4SCN: The
preparation of 2-hydroxy-3-phenoxypropyl thiocyanate was carried out by grinding CMPI
(0.255 g, 1 mmol) and NH4SCN (0.076 g, 1 mmol) in a mortar for 1 min. Next, oxi-
ranylmethyl phenyl ether (0.16 mL, 1 mmol) was added to the mixture and grinding was
continued for an additional 2 min. After completion of the reaction, H2O (5 mL) was added
and the organic layer extracted with Et2O (3 × 5 mL). The combined organic extracts were
dried (Na2SO4). Evaporation of the solvent and chromatography on a short silica gel col-
umn using n-hexane/EtOAc (5/2) as eluent gave 2-hydroxy-3-phenoxypropyl thiocyanate
(0.188 g, 90%).
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