4-ethylphenol

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:

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

Procedure: A solution was prepared by dissolving 105 g of 4-ethylphenol into 500 ml of chloroform. The solution was cooled by ice water bath, followed by dropwise addition of 45 ml of bromine while stirring. The addition was took 1 hour. Then, the reaction mixture was cooled by an ice water bath while stirring for 4 hours, moved into a separatory funnel to wash with water, an aqueous solution saturated with NaCl, 10% water solution of sodium hydrogencarbonate and an aqueous solution saturated with NaCl in turn, and dried with magnesium sulfate anhydride. The solvent in the reactant was distilled off under reduced pressure to yield 173 g of light brown and oily 2-bromo-4-ethylphenol. A solution was prepared The solution was cooled by ice water bath The addition Then, the reaction mixture was cooled by an ice water bath while stirring for 4 hours moved into a separatory funnel to wash with water an aqueous solution saturated with NaCl, 10% water solution of sodium hydrogencarbonate and an aqueous solution saturated with NaCl in turn, and dried with magnesium sulfate anhydride The solvent in the reactant was distilled off under reduced pressure

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

Procedure: In a closed vessel 12.2g (0.1 mol) of p-ethylphenol, 7.2 g (0.1 mol) of 1,2-butylene oxide and 0.8 ml of a 50% aqueous solution of sodium hydroxide were heated at 140° to 145° C for 4 hours in the same way as in Example 1. The reaction mixture obtained was treated in the same way as in Example 1 to afford 14.8 g of 1-(p-ethylphenoxy)-butan-2-ol (compound No. 52) in a yield of 76.3%. The reaction mixture obtained was treated in the same way as in Example 1

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

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

Procedure: Subsequently, 50 ml of acetonitrile, 0.092 mol of β-phenoxyethyl-p-tosylate, and 0.1 mol of p-ethylphenol were placed in a flask equipped with a stirrer. A 48 wt% aqueous solution of caustic soda (0.12 mol equivalent) was added dropwise at an inner temperature of not more than 75° C. while stirring. The mixture was stirred while refluxing for 2 hours. The reaction mixture was allowed to cool. On pouring the reaction mixture at about 40° C. into a methanol-water mixture, crystals precipitated. These crystals were separated by filtration, and then dried to yield 1-phenoxy-2-p-ethylphenoxyethane (m.p., 107°-108° C.). The yield was 98%. equipped with a stirrer The mixture was stirred while refluxing for 2 hours to cool precipitated These crystals were separated by filtration dried

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

Procedure: Subsequently, 50 ml of acetonitrile, 0.092 mol of β-phenoxyethyl-p-tosylate, and 0.1 mol of p-ethylphenol were placed in a flask equipped with a stirrer. A 48 wt% aqueous solution of caustic soda (0.12 mol equivalent) was added dropwise at an inner temperature of not more than 75° C. while stirring. The mixture was stirred while refluxing for 2 hours. The reaction mixture was allowed to cool. On pouring the reaction mixture at about 40° C. into a methanol-water mixture, crystals precipitated. These crystals were separated by filtration, and then dried to yield 1-phenoxy-2-p-ethylphenoxyethane (m.p., 107°-108° C.). The yield was 98%. equipped with a stirrer The mixture was stirred while refluxing for 2 hours to cool precipitated These crystals were separated by filtration dried

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-ethylphenol (25.4 g, 0.21 mol) and sulfuryl chloride (18.5 ml, 0.23 mol) in carbon tetrachloride (40 ml) was stirred under heating at 70° C. for 3 hr. The reaction mixture was diluted with chloroform and washed with water. The organic layer was dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 2-chloro-4-ethylphenol (25.1 g, 77%). washed with water The organic layer was dried over magnesium sulfate the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)