HCID 54570750, compound → HCID 54175977, compound

Participants

Reaction Steps

Preparation of 4-(4-pentylbenzyloxy)-1-(1,5-hexadienyl) benzene ##STR1144## (Compound No. 279 expressed by general formula (1) wherein R1 represents pentyl group, X3 represents --CH2O--, C and D represent 1,4-phenylene ring, l, m, and n are 0, o is 1, p is 2, and R2 and R2 ' are hydrogen atom.) Solution of the 4-(1,5-hexadienyl)phenol (500 mmol) obtained by the same method as in Example 4 in 120 ml of THF was added dropwise to a mixture of sodium hydride (120 mmol), 20 ml of THF, and 50 ml of DMF, and stirred for about 2 hours until generation of hydrogen gas ceased. To this solution was added dropwise a solution of 4-pentylbenzylbromide (45 mmol) in 50 ml of THF at a temperature lower than 0° C. and stirred for further 5 hours. Water in an amount of 100 ml and 100 ml of toluene were added to this solution, and the organic layer was washed with 100 ml of 2M hydrochloric acid and 100 ml of saturated aqueous solution of sodium bicarbonate, washed with water until it became neutral, and then dried with anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure and the residue was recrystallized from ethanol 5 times as much as the residue to obtain 21 mmol of white oily subject compound. NMR spectrum, mass spectrum, IR spectrum, and the values of elementary analysis of this compound well supported its structure.

Provenance & Evidence