Hydroquinone → 4-(6'-Methyloctyloxy)phenol

Reaction equation

[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH3:18])[CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:18][CH:15]([CH2:16][CH3:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1

Participants

Procedure

A 25 ml-flask was charged with 0.637 g of hydroquinone, 1 g of optically active 1-bromo-6-methyloctane, 0.667 g of anhydrous potassium carbonate and 4 ml of N,N-dimethylformamide, and reaction was carried out at 90° C. for 9.5 hours. After the reaction, insoluble substances were recovered by filtration and extracted with ether. The ether layer was washed with water and a saturated aqueous solution of sodium chloride and dried, and ether was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel chromatography to obtain 0.32 g of optically active 4-(6'-methyloctyloxy)phenol.