Bruce A. Hathaway

Comparison of Iodination of Methoxylated Benzaldehydes and Related Compounds using Iodine/Silver Nitrate and Iodine/Periodic Acid

Abstract Iodination of the three methoxybenzaldehydes, four dimethoxybenzaldehydes, vanillin, and piperonal by two methods were compared. Iodine and periodic acid gave better yields for iodination for the methoxybenzaldehydes, whereas iodine and silver nitrate generally gave better yields for the rest of the compounds.

Selective Preparation of 4-(Bromo or Iodo)-2,5-dimethoxybenzonitrile and 2-(Bromo or Iodo)-3,6-dimethoxybenzonitrile from 2,5-Dimethoxybenzaldehyde

Abstract By use of appropriate reactions and sequence of steps, 2,5-dimethoxybenzaldehyde can be converted either to 4-(bromo or iodo)-2,5-dimethoxybenzonitrile or 2-(bromo or iodo)-3,6-dimethoxybenzonitrile.

Oxidation of Benzaldehydes to Benzoate Esters Using Household Bleach and Sodium Iodide in Alcohol Solvents

Abstract Various substituted benzaldehydes were converted into benzoate esters with household bleach and sodium iodide in an alcohol solvent. The reaction works best with methanol. Only 4-chlorobenzaldehyde, 3-nitrobenzaldehyde, and 4-nitrobenzaldehyde reacted completely with 1-propanol under these conditions. [Supplementary materials are available for this article. Go to the publishers online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] GRAPHICAL ABSTRACT

1,2-Diiodo-4,5-dimethyl­benzene

The structure of the title compound, C8H8I2, conforms closely to the mm2 symmetry expected for the free molecule and is the first reported structure of a diiododimethylbenzene. Repulsion by neighboring I atoms and the neighboring methyl groups opposite to them results in a slight elongation of the molecule along the approximate twofold rotation axis that bisects the ring between the two I atoms. In the extended structure, the molecules form inversion-related pairs which are organized in approximately hexagonal close-packed layers and the layers then stacked so that molecules in neighboring layers abut head-to-tail in a manner that optimizes dipole–dipole interactions.

1-Nitro-3-[(phenylsulfonyl)methyl]benzene

In the course of our work to prepare inhibitors of the enzyme dihydrofolate reductase, we desired to prepare sulfone analogues of some previously reported sulfides [1, 2].[...]

1-(4-Nitrophenyl)-1-octyne

Following the procedure of Takahashi, et al (1), to a mixture of 1-iodo-4-nitrobenzene (7.76 mmol, 1.90g) and 1-octyne (9.3 mmol, 1.023g) in diethylamine (40 mL) are added bis[triphenylphosphine]palladium dichloride (0.2mmol, 0.14g) and copper(I) iodide (0.1mmol, 0.01g).[...]

4,4'-(4,5-dimethyl-1,2-phenylene)bis(2-methylbut-3-yn-2-ol): structural variation in vicinal dialkynols.

The structure of the title compound, C(18)H(22)O(2), contains two non-equivalent molecules which differ primarily in the location of the -OH groups on opposite sides or on the same side of the molecular plane. Inversion-symmetric pairs of molecules form intermolecular O-H...O hydrogen-bonded tetrameric synthons that link non-equivalent molecules into an approximately square double layer parallel to (-102). Recently reported fluorinated analogues [Kane, Meyers, Yu, Gerken & Etzkorn (2011). Eur. J. Org. Chem. pp. 2969-2980] have significantly different structures of varying complexity that incorporate intramolecular hydrogen bonding and suggest that further study of structure versus substituents in vicinal dialkynols could be fruitful.

1-Ethyl 2,2-dimethyl 3-(1,3-benzodioxol-5-yl)propane-1,2,2-tricarboxylate.

The molecular structure of the title triester compound, C(17)H(20)O(8), consists of a benzodioxole fused-ring system, an ethoxycarbonylmethyl group and two methoxycarbonyl groups arranged around a tetrahedral carbon center. Unlike similar triesters, which are oils, the title compound crystallizes at room temperature as interdigitated bilayers of triester molecules, with short O...H contacts from the methylene H atoms of benzodioxole to the carbonyl O atom of the ethoxycarbonylmethyl group and to a ring O atom of the benzodioxole group of a neighboring molecule within the bilayer. The persistence of these short C-H...O interactions from the activated H atoms of the benzodioxole ring at both 100 and 300 K indicate that they help provide the stabilization necessary for crystallization from the oil.

3-[(Benzylsulfonyl)methyl]aniline hydrochloride

In the course of our work to prepare inhibitors of the enzyme dihydrofolate reductase, we desired to prepare sulfone analogues of some similar sulfides [1, 2].[...]

4-(Benzylthio)acetophenone

During the course of our research on preparing parallel dipole-aligned crystals [1-2], we needed to prepare the previously unreported compound 4-benzyl-sulfonylacetophenone.[...]