2-Mercapto-4-heptanol is a relatively new flavour compound that was recently approved as an ingredient by the Flavour and Extract Manufacturers’ Association in 2013. Its synthesis, which we have accomplished in four-steps, involved firstly a Grignard reaction of n-butanal with allylmagnesium chloride to prepare 1-hepten-4-ol. This was epoxidised and then converted to 1,2-epithio-4-heptanol, reduction of which with LiAlH4 gave the target compound in an overall yield of about 54%.
RoweD.J., Advances in flavours and fragrances – from the sensation to the synthesis, SwiftK.A.D., ed. The Royal Society of Chemistry, Cambridge, 2002, pp. 202–206.
2.
WidderS., Sabater LüntzelC., DittnerT., and PickenhagenW., J. Agric. Food Chem., 2000, 48, 418.
3.
EngelK.-H., and TresslR., J. Agric. Food Chem., 1991, 39, 2249.
NaefR., VelluzA., and JaquierA., J. Agric. Food Chem., 2008, 56, 517.
9.
StarkenmannC., and NiclassY., J. Agric. Food Chem., 2011, 59, 3358.
10.
MarnettL.J., CohenS. M., FukushimaS., GooderhamN. J., HechtS. S., RietjensL. M. C. M., SmithR. L., AdamsT. B., HallaganJ. B., HarmanC., McGowenM. M., and TaylorS. V., Food Technol., 2013, 67, 38.
11.
VermeulenC., and CollinS., J. Agric. Food Chem., 2003, 51, 3618.
12.
SiddavatamN., MarthaK., VankaK. R., and DasB., Eur. J. Chem., 2012, 3, 337.
13.
LiangS., SunB., YangS., LiuY., TianH., LiuY., and ChenH., J. Chem. Res., 2014, 38, 343.
14.
WickelS.M., CitronC. A., and DickschatJ. S., Eur. J. Org. Chem., 2013, 2906.
