Salicylic sodium salt

Sodium chlorate Sodium chloride Sodium chlorite Sodium chloroacetate Sodium chromate Sodium citrate Sodium cyanate Sodium cyanide Sodium terricyanide Sodium terrocyanide Sodium fluoride Sodium fluorosilicate Sodium hydride Sodium hydrosulflde Sodium hydroxide Sodium hypochlorite Sodium lactate Sodium nitrate Sodium oleate Sodium oxalate Sodium perborate Sodium percarbonate Sodium perchlorate Sodium peroxide Sodium persulfate Sodium phenolate Sodium phosphate Sodium salicylate Sodium salts Sodium silicate Sodium stannate Sodium sulfate Sodium sulfide Sodium sulfite Sour crude oil (1050LF)... 

Sodium salicylic acid. See Sodium salicylate Sodium salt of crosslinked carboxymethyl ether cellulose. See Croscarmellose sodium Sodium salt of sulfonated naphthalene-formaldehyde condensate. See Sodium polynaphthalene sulfonate Sodium sarcosinate... 

When the phenol contains a carboxylic acid group, e.g., m- or p-hydroxy-benzoic acid, the acetylated derivative will of course remain in solution as the sodium salt, but is precipitated when the solution is subsequently acidified. Salicylic acid, however, cannot be acetylated under these conditions. 

Section 24 10 The Kolbe-Schmitt synthesis of salicylic acid is a vital step m the preparation of aspirin Phenols as their sodium salts undergo highly regioselective ortho carboxylation on treatment with carbon dioxide at elevated temperature and pressure... 

Kolbe-Schmitt reaction (Section 24 10) The high pressure re action of the sodium salt of a phenol with carbon dioxide to give an o hydroxybenzoic acid The Kolbe-Schmitt reac tion IS used to prepare salicylic acid in the synthesis of as pinn... 

Perhaps the most widely known compound prepared from phenol is aspirin. If phenol, sodium hydroxide, and carbon dioxide are heated together under pressure, salicylic acid is formed (as the sodium salt) ... 

The acid itself (or the sodium salt) is a valuable drug in the treatment of arthritis. But the most widely known derivative of salicylic acid is aspirin, which has ihe following structure ... 

C7Hft03 69-72-7) see Acetylsalicylic acid Balsalazide sodium Flavoxate Hydroxyethyl salicylate Mesalazine Salazosulfapyridine Salsalate salicylic acid sodium salt... 

CjHjNaO, 113-24-6) see Flurbiprofen sodium salicylate see under salicylic acid sodium salt sodium 3-sulfobenzoate... 

An additional useful test is to distil the acid or its sodium salt with soda lime. Heat 0.5 g. of the acid or its sodium salt with 0 2 g. of soda lime in an ignition tube to make certain that there is no explosion. Then grind together 0 5 g. of the acid with 3 g. of soda lime, place the mixture in a Pyrex test-tube and cover it with an equal bulk of soda hme. Fit a wide dehvery tube dipping into an empty test-tube. Clamp the tube near the mouth. Heat the soda lime first and then the mixture gradually to a dull-red heat. Examine the product this may consist of aromatic hydrocarbons or derivatives, e.g., phenol from salicylic acid, anisole firom anisic acid, toluene from toluic acid, etc. 

Valproic acid/salts Losartan Meglumine antimoniate Piroxicam Procainamide Salicylates Sodium stibogluconate Zalcitabine... 

Technically important dyes are salicylic acid derivatives that function as chrome mordant dyes for wool. Thus Cl Mordant Blue 1 (6.187) is made by the aldehyde synthesis from 2,6-dichlorobenzaldehyde and 2-hydroxy-3-methylbenzoic (o-cresotinic) acid in concentrated sulphuric acid. Oxidation of the leuco base is achieved by the addition of sodium nitrite. On wool the product, which is isolated as the sodium salt, is a dull maroon colour, changing to a bright blue on treatment with a chromium salt. Some dyes of this type, such as Cl Mordant Violet 1 (6.188), also contain a basic group. This compound is also prepared by the aldehyde route. 

Since, in Kolbe s synthesis, as here described, the mono-sodium salicylate reacts to some extent with unchanged sodium phenoxide, producing the di-sodium salt, part of the phenol is liberated and excluded from the reaction. The reaction proceeds to completion if the sodium phenoxide is heated to about 150° for a long time, with carbon dioxide under pressure in the autoclave. This is the technical method of Schmitt. 

Indians. The active principle, salicin, was isolated in 1829. It is chemically converted to the active principle, salicylic acid, in the intestine and liver. The chemically modified acetylsalicylic acid was first marketed in 1899 as aspirin. Salicin is also found in meadowsweet (Filipenduia ulmaria, then referred to as Spireaea ulmaria), from which the name aspirin derives (acetyl sp/r/c acid). The sodium salt of salicylic acid has the drawback of producing gastrointestinal irritation, but acetylsalicylic acid is well tolerated. 

Pharmacology Olsalazine sodium is a sodium salt of a salicylate compound that is effectively bioconverted to 5-aminosalicylic acid (mesalamine 5-ASA), which has anti-inflammatory activity in ulcerative colitis. Approximately 98% to 99% of an oral dose will reach the colon, where each molecule is rapidly converted into 2 molecules of 5-ASA by colonic bacteria. The liberated 5-ASA is absorbed slowly, resulting in very high local concentrations in the colon. 

A number of 5//-l,4-benzodioxepin-ones and -diones have been prepared (72HC(26)319, p. 339). The reaction of the sodium salt of salicylic acid with 2-chloroethanol gave (269) (75BSF(2)277) and treatment of the methyl ester of 2-acetyl-6-chloro-3,5-dimethoxyphenoxyacetic acid with 3M hydrochloric acid gave (270). The dione (271) was prepared by heating 2-carboxy-5,6-dimethoxyphenoxyacetic acid in acetic anhydride and (272) was prepared from chloroacetylsalicylic acid. 

Methyl -propyl ketone, 340 Methyl pyridines, purification of, 177-179 N-Methylpyrrole, 837, 838 Methyl red, 621, 625 sodium salt of, 626 Methyl salicylate, 780,782 Methyl sulphite, 304 2-Methylthiophene, 836 Methyl p-toluenesulphonate, 825 Methylurea, 968, 969 Methylene bromide, 300 Methylene chloride, purification of, 176 3 4-Methylenedioxycinnamic acid, 711, 719... 

This curve represents the titration curve obtained by titrating the sodium salt of 6y6 -bicreosol II) with salicylic acid. 

In general a phenol will undergo direct carboxylation of the nucleus when the dry sodium salt is heated under pressure with carbon dioxide (the Kolbe-Schmidt reaction). Addition of the weakly electrophilic carbon dioxide is promoted by electron release from the oxyanionic site. With phenol itself the ultimate product is salicylic acid (o-hydroxybenzoic acid) predominantly ortho attack may be attributable to stabilisation of the transition state through chelation. 

As an example of 1 2 chromation by the chromium(m) salicylic acid method [19], the sodium salt of the azo dye obtained from diazotized 1-amino-2-hydroxy-5-nitrobenzene and acetoacetic acid 3-sulfonamidophenylamide in water and a solution of chromium(m) sodium potasium salicylate are refluxed for several hours. The 1 2 chromium complex 11 is precipitated at below pH 4. It is a yellow brown powder, which is soluble in hot water with a greenish yellow color. 

We have already seen how salicylic acid can be made by reaction of the sodium salt of phenol (PhONa) with C02. More important than these reactions is chloromethylation, a way of adding a single carbon atom at the alcohol oxidation level. A combination of formaldehyde (CH2=0) and HCl provides the one-carbon electrophile. 

Carboxylation. The introduction of carboxyl groups into the structures of phenols and naph-thols produces some important dye intermediates, including salicylic acid and (3-oxynaphthoic acid (BON acid). This process is conducted under pressure at elevated temperatures using the sodium salts of phenols/naphthols and in the case of (3-naphthol, the carboxyl group enters... 

The only practical methods for the preparation of o-chloro-benzoyl chloride to be found in the literature consist in the treatment of o-chlorobenzoic acid with phosphorus penta-chloride1 or thionyl chloride.2 It has, however, also been formed by distilling salicylic acid or its sodium salt with phosphorus pentachloride,3 and by heating the dichloride of o-sulfobenzoic acid.4... 

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