Selective Acceptorless Conversion of Primary Alcohols to Acetals and Dihydrogen
nal standards. Signal identity was confirmed by GC/MS. For-
mation of acetals was further confirmed by 1H NMR and
ESI-MS. The amounts of benzyl alcohol and benzaldehyde
were determined by HPLC. HPLC conditions were: flow
rate=1 mLminÀ1, injection volume=20 mL, detector wave-
length=254 nm. Mobile phase was 70:30 acetonitrile:H2O.
Samples were prepared as follows: the reaction mixture was
cooled down, treated with hexane (10 mL) and left at
À208C for several days to precipitate the catalyst. The
hexane solution was extracted with 50 mL of acetonitrile
(sample A). Sample B was prepared by two-fold dilution of
the sample A. Retention times: benzyl alcohol, 2.6 min;
benzaldehyde, 3.2 min; dibenzyl ether, 6.6 min; benzalde-
hyde dibenzyl acetal, 11.9 min. After conducting HPLC
measurements, samples A and B were unified, volatiles
were evaporated and the yields of dibenzyl ether and ben-
zaldehyde dibenzyl acetal were determined by 1H NMR
with mesitylene as the internal standard.
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Acknowledgements
This research was supported by the European Research
Council under the FP7 framework (ERC No. 246837), by the
Israel Science Foundation, by the MINERVA foundation and
by the Kimmel Center for Molecular Design. D.M. is the
Israel Matz Professorial Chair of Organic Chemistry.
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