Hydroquinone methanol compound

Amides, some carboxylic acids, some sulfoxides Some carboxylic acids, hydroquinones Nitro compounds, esters, bromo compounds, some sulfoxides, sulfones, sulfilimines, anilines Same as methanol... 

THE HYDROQUINONE METHANOL AND HYDROQUINONE HYDROGEN CYANIDE CLATHRATE COMPOUNDS... 

Figure 4 shows the transition temperature of the hydroquinone clathrate compound plotted against the square of the dipole moment of the guest molecule. The data on the hydrogen sulphide, methanol and hydrogen cyanide compounds are those of the heat capacity anomalies. The transition temperature of the acetonitrile compound, if it exists, lies above the room temperature. One finds a good proportionality between the transition temperature and the square of the dipole moment. 

Reactions with Organic Compounds. Tetrafluoroethylene and OF2 react spontaneously to form C2F and COF2. Ethylene and OF2 may react explosively, but under controlled conditions monofluoroethane and 1,2-difluoroethane can be recovered (33). Benzene is oxidized to quinone and hydroquinone by OF2. Methanol and ethanol are oxidized at room temperature (4). Organic amines are extensively degraded by OF2 at room temperature, but primary aHphatic amines in a fluorocarbon solvent at —42°C are smoothly oxidized to the corresponding nitroso compounds (34). 

The reaction mixture was removed from the vessel and distilled at a pressure of 30-60 mm, and a bath temperature of 30°C to 50°C until the methanol had all been removed. The extremely viscous tarry residue remaining in the still pot was given a very crude distillation, the distillate boiling at B2°C to 1 32°C/2 mm. In an attempt to purify this distillate by a more careful distillation, 5.3 g of a liquid distilling from 53°C to 150°C/5 mm was collected. At this point, much solid sublimate was noted not only in this distillate but in the condenser of the still. 7 g of the solid sublimate was scraped out of the condenser of the still. Recrystallization of the sublimate from ethyl acetate containing a small amount of petroleum ether gave beautiful crystals melting at 175°C to 177°C (5 g). Infrared analysis confirmed that this compound was hydroquinone (9% conversion). 

The last of the butyl isomers, the tert-butyl compound, was made from a much more obvious starting material. This is the commercially available tert-butyl hydroquinone. It was methylated in sodium hydroxide with methyl iodide, and then carried through the above sequence (benzaldehyde. mp 124 °C from cyclohexane, nitrostyrene, yellow crystals from methanol, mp 95-96.5 °C, and lithium aluminum hydride reduction) to give 2,5-dimethoxy-4-(l,l-dimethylethyl)amphetamine hydrochloride (DOTB, mp 168 °C). Rats trained in a process called the Sidman Avoidance Schedule gave behavior that suggested that DOTB had no activity at all, and in human trials, doses of up to 25 milligrams were totally without effect. 

Fig. 6.7. Separation of a mixture of polar and nonpolar aromatic compounds by CEC. Conditions capillary 27 cm x 75 pm i.d.For details on monolith column see Fig. 6.6 mobile phase 1 3 methanol/acetonitrile, 30kV, 25°C, injection 10 kV for 3s UV- detection at 200 nm. (Reprinted with permission of authors from [32]). Peaks pyrene 1, phenanthrene 2, anthracene 3, phenol 4, hydroquinone monomethylether 5, 2-naphtol 6, catechol 7, hydroquinone 8, resorcinol 9.

Similar solubility behavior of polyhydroxy compounds was shown in fused acetates by Burton and Crowell. Burton observed that solubility of several organic compounds at 200°C, in (Li, Na, K) acetate eutectic (mp 180°C) increases with the number of hydroxyl groups and with acidity. In weight percent the following approximate solubilities were determined methanol, 0.05% 2,4-dinitroaniline and 4-nitroaniline, < 0.5% hydroquinone and resorcinol, 1% 2-amino-2-hydroxymethyl-l, 3-propanediol and 2-amino-2-methyl-l,3-propanediol, I0% trimethylolethane and pentaerythritol were miscible in all proportions above their melting points. 

Hydroquinone, p-C6H4(OH)2, also known as quinol in the older literature) exists in three polymorphic forms (or crystalline modifications). a-Hydroquinone is the stable form at room temperature, whereas the metastable monoclinic y-form can be prepared by sublimation or rapid evaporation of a solution in ether. Crystallization of hydroquinone from a common solvent such as methanol generally yields a clathrate with guest solvent inolecules trapped inside cavities of the (3-hydroquinone host lattice.". The existence of the (3 polymorph of hydroquinone (empty P-hydroquinone clathrate), which can be obtained by crystallization from n-octane, was reported in 1981. Described in this article are the structural features of these compounds, and some recent developments are also covered. 

Qathrate compounds are of this type molecules of one substance are trapped in the open structure of molecules of another. Hydroquinone forms clathrate compounds with SO2 and methanol, for example. Urea and thiourea also have the property of forming complexes, known as adducts, with certain types of hydrocarbons. In these cases molecules of the hydrocarbons fit into holes or channels in the crystals of urea or thiourea the shape and size of the molecules determine whether they will be adducted or not. 

In summary, an unusual structural change of a vinylene-bridged ferrocene-hydroquinone compound, FCCHCHBQH2, was observed to occur by two-electron oxidation and two-proton elimination in methanol. The oxidation product, FcCHCBQH, which includes an allene and a quinonoid structure, exhibited a unique proton response, leading to an exchange of the magnetic properties. 

---