Sodium bicarbonate reaction with

Add 4 4 g. of recrystaUised -phenylhydroxylamine to a mixture of 20 ml. of concentrated sulphuric acid and 60 g. of ice contained in a 1 litre beaker cooled in a freezing mixture. Dilute the solution with 400 ml. of water, and boil until a sample, tested with dichromate solution, gives the smell of quinone and not of nitrosobenzene or nitrobenzene (ca. 10-15 minutes). Neutralise the cold reaction mixture with sodium bicarbonate, saturate with salt, extract twice with ether, and dry the ethereal extract with anhydrous magnesium or sodium sulphate. Distil off the ether p-aminophenol, m.p. 186°, remains. The yield is 4-3 g. 

Dissolve the amine-containing molecule to be thiolated at a concentration of lOmg/ml in cold (4°C) 1M sodium bicarbonate (reaction buffer). For proteins, dissolve them in deionized water at a pH of 7.0-7.5, at room temperature. Note The presence of some buffer salts, like phosphate or carbonate, is incompatible with silver nitrate. 

At 70°C there were added BBr3 with the injector into a solution of l-methyl-2-(4-methoxy-phenyl)-6-methoxy-l-ethylindole in water free methylene chloride. After 30 min the cold bath was removed and the mixture stirred overnight. The reaction mixture is carefully poured into a saturated sodium bicarbonate solution with ice cooling. The product is extracted three times with ethyl acetate, the combined organic extracts washed with sodium bicarbonate solution and water, dried and the solvent removed on a rotary evaporator. The 3-methyl-2-(4-hydroxyphenyl)-6-hydroxy-l-ethylindole was produced, melting point 142-143°C. 

To a solution of HTI (5.16 g, 13 mmol) in methanol (60 ml) was added phenylpropyne (11.6 g, 10 mmol) and the solution was refluxed for 96 h. The reaction mixture was treated with a saturated solution of sodium bicarbonate, extracted with dichloromethane (3 x 50 ml), dried and concentrated to an oil this was hydrolysed in 2N sodium hydroxide solution to give a-methylphenylacetic acid (9.9 g, 66%) b.p. 262°C. 

At this point cyclopropylcarbinol has been completely converted into a mixture of products containing ca. 80% cyclobutanol, 8% 3-butene-l-ol, and several additional products observable by GLC analysis in varying amounts. About 95-97% pure cyclobutanol (60-65% yield) can be obtained if the reaction mixture is neutralized with sodium hydroxide and sodium bicarbonate, saturated with magnesium sulfate, extracted with ether, and fractionally distilled on an efficient distillation column. The remaining impurities are extremely difficult to remove. 

Under argon, to a solution of (2 )-(+)-BINOL (0.132 g, 0.46 mmol) over 4 A molecular sieves (0.732 g) in methylene chloride (2.8 mL) was added Ti(Ot-Pr)4 (0.069 mL, 0.23 mmol). The resulting deep solution was stirred at ambient temperature for 1.5 h then treated with a solution of the aldehyde (0.5 g, 2.9 mmol) in methylene chloride (1.3 mL). The solution was stirred for 2 min, cooled to 0 °C, treated with tlie allylstannane (1.15 g, 3.2 mmol) over 2 min, and maintained at this temperature for 4.5 h. The reaction was then quenched with saturated sodium bicarbonate, extracted with EtOAc (3x), dried over magnesium sulfate, and concentrated in vacuo. The crude product was purihed via hash chromatography using EtOAc hexanes (1 9) to afford 0.495 g (70%) of the an/z-alcohol and 28 mg (4%) of the 5yn-alcohol as colorless oils. 

ARTIFICIAL ANT OIL (98-01-1) Forms explosive mixture with air (flash point 140°F/60°C). Strong acids or strong bases may cause polymerization. Violent reaction with strong acids, alkalis, sodium bicarbonate. Incompatible with ammonia, aliphatic amines, alkanolamines, aromatic amines, oxidizers. Attacks many plastics and coatings. 

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