10-bromodecan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,6-bis(dimethylamino)acridine (1.0 millimole) is dissolved in DMF (100 ml) containing 1.1 equivalent of tertiary amine base. To this is added 10-hydroxy-1-bromo decane (1.1 millimole), and the mixture is heated to reflux. When monitoring by TLC shows no remaining 3,6-bis(dimethylamino)acridine, the reaction is cooled and the 10-N-(10-hydroxyl-decyl)-3,6-bis(dimethylamino)acridine is isolated (0.75 millimoles). the mixture is heated to reflux the reaction is cooled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,2-dimethyl-propionic acid 10-bromodecyl ester was prepared in 85% yield by treatment of 10-bromodecan-1-ol with trimethylacetyl chloride in the presence of pyridine and 4-dimethylaminopyridine at room temperature in dithlcromethane. After 18 hrs, the reaction was quenched by the addition of dilute hydrochloric acid worked up and filtered through silica to provide 2,2-dimethyl-propionic acid 10-bromodecyl ester. the reaction was quenched by the addition of dilute hydrochloric acid filtered through silica to provide 2,2-dimethyl-propionic acid 10-bromodecyl ester

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 87.8 g (0.50 mol) of 1,10-decanediol, 165.1 g of 48% strength hydrobromic acid and 2.5 l of high-boiling petroleum ether (b.p. 100-140° C.) were heated under reflux with vigorous stirring for 4 hours. A further 80.0 g of 48 strength hydrobromic acid were added, and the mixture was boiled for 5 hours. After cooling to 30° C., the phases were separated. The organic phase was washed first with a solution of 100 g of Na2CO3 in 500 ml of water and then with 2×500 ml of water. Removal of the solvent was followed by chromatography on 700 g of silica gel. The byproduct 1,10-dibromodecane was eluted with cyclohexane/diethyl ether (20:1). Chromatography with cyclohexane/diethyl ether (2:1) afforded 103.9 g (0.44 mol, 87%) of 10-bromo-1-decanol. under reflux the mixture was boiled for 5 hours the phases were separated The organic phase was washed first with a solution of 100 g of Na2CO3 in 500 ml of water Removal of the solvent The byproduct 1,10-dibromodecane was eluted with cyclohexane/diethyl ether (20:1)

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 87.8 g (0.50 mol) of 1,10-decanediol, 165.1 g of 48% strength hydrobromic acid and 2.5 l of high-boiling petroleum ether (b.p. 100-140° C.) were heated under reflux with vigorous stirring for 4 hours. A further 80.0 g of 48 strength hydrobromic acid were added, and the mixture was boiled for 5 hours. After cooling to 30° C., the phases were separated. The organic phase was washed first with a solution of 100 g of Na2CO3 in 500 ml of water and then with 2×500 ml of water. Removal of the solvent was followed by chromatography on 700 g of silica gel. The byproduct 1,10-dibromodecane was eluted with cyclohexane/diethyl ether (20:1). Chromatography with cyclohexane/diethyl ether (2:1) afforded 103.9 g (0.44 mol, 87%) of 10-bromo-1-decanol. under reflux the mixture was boiled for 5 hours the phases were separated The organic phase was washed first with a solution of 100 g of Na2CO3 in 500 ml of water Removal of the solvent The byproduct 1,10-dibromodecane was eluted with cyclohexane/diethyl ether (20:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,2-dimethyl-propionic acid 10-bromodecyl ester was prepared in 85% yield by treatment of 10-bromodecane-1-ol with trimethylacetyl chloride in the presence of pyridine and 4-dimethylaminopyridine at room temperature in dithlcromethane. After 18 hrs, the reaction was quenched by the addition of dilute hydrochloric acid worked up and filtered through silica to provide 2,2-dimethyl-propionic acid 10-bromodecyl ester. the reaction was quenched by the addition of dilute hydrochloric acid filtered through silica to provide 2,2-dimethyl-propionic acid 10-bromodecyl ester

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,2-dimethyl-propionic acid 10-bromodecyl ester was prepared in 85% yield by treatment of 10-bromodecane-1-ol with trimethylacetyl chloride in the presence of pyridine and 4-dimethylaminopyridine at room temperature in dithlcromethane. After 18 hrs, the reaction was quenched by the addition of dilute hydrochloric acid worked up and filtered through silica to provide 2,2-dimethyl-propionic acid 10-bromodecyl ester. the reaction was quenched by the addition of dilute hydrochloric acid filtered through silica to provide 2,2-dimethyl-propionic acid 10-bromodecyl ester