Research Article: Di-tert-butyl (2R,3R)-2-{[(2E)-3-(4-acet­yloxy-3-meth­oxy­phen­yl)prop-2-eno­yl]­oxy}-3-hy­droxy­butane­dioate

Date Published: March 01, 2012

Publisher: International Union of Crystallography

Author(s): Josh L. Hixson, Dennis K. Taylor, Seik Weng Ng, Edward R. T. Tiekink.


In the title mol­ecule, C24H32O10, one tert-butyl ester group is folded towards the central benzene ring while the other is directed away. The acetyl group is almost perpendicular to the benzene ring to which it is connected [C—C—O—C torsion angle = 90.4 (12)°]. The conformation about the ethene bond [1.313 (7) Å] is E. The atoms of the benzene ring and its attached ester group and part of the hy­droxy tert-butyl ester side chain are disordered over two sets of sites in a 50:50 ratio. Linear supra­molecular chains along the a axis mediated by hy­droxy–carbonyl O—H⋯O hydrogen bonds feature in the crystal packing. The same H atom also partakes in an intra­molecular O—H⋯O inter­action.

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For background to the formation of the odorant 4-ethyl­guaiacol with relevance to the wine industry, see: Chatonnet et al. (1992 ▶); Hixson et al. (2012 ▶); Ong & Nagel (1978 ▶); Nagel & Wulf (1979 ▶); Zhao & Burke (1998 ▶). For the preparation and characterization of 1-O-acetyl ferulic acid; see: Zhao & Burke (1998 ▶); Hosoda et al. (2001 ▶).