Pyrogallol-13-dimethyl ether

Carbon tetrachloride, 32, 27 37, 8 Carbonylation, of pyrogallol-1,3-dimethyl ether with hexamethylenetetramine, 31, 92... 

Carbomethoxybenzaldehyde, 30, 100 5-Carbomethoxy valeryl chloride, 38, 39 Carbon disulfide, 30, 57 39, 8, 78 Carbonic acid, trithio-, bis(carboxy-methyl) ester, 39, 77 Carbonic-carboxylic anhydrides, 37, 21 Carbon monoxide, 34, 14 Carbon oxysulfide, 32, 103 Carbon tetrachloride, 32, 27 37, 8 Carbonylation, of pyrogallol-1,3-dimethyl ether with hexamethylenetetramine, 31, 92 of pyrrole with dimethylformamide,... 

Compounds with free para positions and blocked ortho positions couple at the />-carbon atoms. Pyrogallol-1,3-dimethyl ether (IX) gives the stable coerulignone (X) in excellent yields (Figure 6). 

Figure 6. Formation of coerulignone X) from pyrogallol-1,3-dimethyl ether IX)...

Pyridine, 3-amino, 30, 3 5-ETHYL-2-METHYL, 30, 41 4-Pyrimidol, 2,6-diamino-, 32, 45 Pyrogallol-1,3-dimethyl ether, 31, 92 Pyrolysis, of, V-a.zo-bis- -cyclohexane-nitrile to l,l -dicyano-l,l -bicyclo-hexyl, 32, 48... 

A well-stirred (Notes 1 and 2) mixture of 740 ml. of glycerol and 216 g. of boric acid, in a 2-1. three-necked round-bottomed flask fitted with a thermometer and a condenser for downward distillation, is dehydrated by heating in an oil bath to exactly 170°. This temperature is maintained for 30 minutes and then allowed to drop. When the temperature has fallen to 150°, a mixture of 154 g. (1 mole) of pyrogallol-1,3-dimethyl ether and 154 g. (1.1 moles) of hexamethylenetetramine (Note 3) is added as rapidly as possible through the neck holding the thermometer. The temperature drops to approximately 125°. Rapid heating... 

Eastman Kodak Company white label grade pyrogallol-1,3-dimethyl ether was used. A larger excess of hexamethylenetetramine in a small trial run did not improve the yield. 

This procedure is a modification of the method described by Manske and coworkers.4 Syringic aldehyde has also been obtained by numerous other procedures from pyrogallol-1,3-dimethyl ether M.v,a and from gallic acid.9 1CU1... 

Pyrogallol-1,3-dimethyl ether (3 in Fig. 6.6.1) is demethylated to pyrogallol-l-methyl ether (4) which in turn is demethylated to pyrogallol (5) by the NE treatment. The rates for demethylating 3 to 4 and 4 to 5 (Fig. 6.6.1) were found to be greater than the rate for demethylating guaiacol to catechol, as shown... 

Fig.6.6.9. Gas chromatogram of NE products. 1 Guaiacol 2 catechol 3 pyrogallol-1,3-dimethyl ether 4 pyrogallol-l-methyl ether 5 pyrogallol 6 internal standard (bibenzyl) 7 diphenyl ether...

Applying the same GC separation conditions described above, calibration curves are made for guaiacol, catechol, pyrogallol-1,3-dimethyl ether, pyrogallol-l-methyl ether, and pyrogallol using the authentic compounds. For each compound, a linear relationship is established between (Wp/W ) and (Ap/A ), as shown in Eq. (1). 

SYNS ALDRICH 1,3-DIMETHYL PYROGALLATE PYROGALLOLDIMETHYLETHER PYROGALLOL-1,3-DIMETHYL ETHER SYRINGOL... 

Duff heated glycerol with boric acid at 170° until no more water was eliminated) added 25 g. each of a phenol and hexamine, heated at 170° for 15 min., and isolated the chelated o-hydroxy aldehyde by steam distillation. For several phenols, yields were in the range 2-8.5 g. Pyrogallol-1,3-dimethyl ether is substituted in the para position to give syringic aldehyde (I) in 31-32% yield. W. Baker applied to... 

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