4-(chloromethyl)phenol

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:

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

Procedure: A solution of p-chloromethyl phenol in acetonitrile (Example 12) was reacted with equimolar sodium cyanide in excess methanol (800 parts methanol/mole sodium cyanide) and the reaction mixture was refluxed for one hour. The oil after solvent evaporation (washed as in Experiment 18) was fractionated to yield 45% of α-cyano-p-cresol (b.p. 150°-155°/1 mm. of mercury; M.P. 68°-70°). Infrared spectra confirmed the identity of the product. the reaction mixture was refluxed for one hour The oil after solvent evaporation (washed as in Experiment 18)

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

Procedure: A solution of p-chloromethyl phenol in acetonitrile (Example 12) was reacted with equimolar dimethyl amine and equimolar 2,4-pentanedione by stirring together for 1 hour. The reactive mixture was diluted with water, acidified with hydrochloric acid, extracted with ether, and then the ether extract was dried with sodium sulfate. The residual oil was triturated with benzene to yield 78% of 3(4' hydroxybenzyl)-2,4-pentanedione, M.P. 93°-94.5° C. Infrared and nuclear magnetic resonance spectra confirmed the identity of the product. extracted with ether the ether extract was dried with sodium sulfate The residual oil was triturated with benzene

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

Procedure: Equimolar quantities of p-chloromethylphenyl chloroformate and dimethyl formamide were reacted at room temperature for one hour in acetonitrile (590 parts acetonitrile for every mole of dimethyl formamide or p-chloromethylphenyl chloroformate). Equimolar quantities of methanol were then added to the immonium salt mixture, and the solution was then stirred for about one half hour (with cooling) at 25°-30° C. (with cooling) at 25°-30° C.

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1.2 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril, 1.17 g of potassium carbonate and 20 ml of hexamethylphosphoric triamide was added 651 mg of 4-hydroxybenzyl chloride and the mixture was stirred at 90° C. for 2.5 hours. The reaction mixture was poured into a large amount of water and extracted with chloroform. After washing with water, the extract was dried over anhydrous sodium sulfate. Chloroform was distilled off and the residue was purified through silica gel column chromatography to give 0.3 g of 6-[4-(4-hydroxybenzyl)-1-piperazinyl]-3,4-dihydrocarbostyril. extracted with chloroform After washing with water the extract was dried over anhydrous sodium sulfate Chloroform was distilled off the residue was purified through silica gel column chromatography

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

Procedure: A solution of p-chloromethyl phenol in acetonitrile (Example 12) was reacted with equimolar sodium cyanide in excess methanol (800 parts methanol/mole sodium cyanide) and the reaction mixture was refluxed for one hour. The oil after solvent evaporation (washed as in Experiment 18) was fractionated to yield 45% of α-cyano-p-cresol (b.p. 50°-155°/1 mm. of mercury; M.P. 68°-70°). Infrared spectra confirmed the identity of the product. the reaction mixture was refluxed for one hour The oil after solvent evaporation (washed as in Experiment 18)

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

Procedure: A solution of p-chloromethyl phenol in acetonitrile (Example 12) was reacted with equimolar dimethyl amine and equimolar 2,4-pentanedione by stirring together for one hour. The reactive mixture was diluted with water, acidified with hydrochloric acid, extracted with ether, and then the ether extract was dried with sodium sulfate. The residual oil was triturated with benzene to yield 78% of 3(4' hydroxybenzyl)-2,4-pentanedione, M.P. 93°-94.5°C. Infrared and nuclear magnetic resonance spectra confirmed the identity of the product. extracted with ether the ether extract was dried with sodium sulfate The residual oil was triturated with benzene

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

Procedure: Equimolar quantities of p-chloromethylphenyl chloroformate and dimethyl formamide were reacted at room temperature for one hour in acetonitrile (590 parts acetonitrile for every mole of dimethyl formamide or p-chloromethylphenyl chloroformate). Equimolar quantities of methanol were then added to the immonium salt mixture, and the solution was then stirred for about one half hour (with cooling) at 25°-30°C. (with cooling) at 25°-30°C.