Phenol → 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

反応式

[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl[C:13]([CH3:21])([CH2:15][CH2:16][C:17](Cl)([CH3:19])[CH3:18])[CH3:14]>>[CH3:14][C:13]1([CH3:21])[CH2:15][CH2:16][C:17]([CH3:19])([CH3:18])[C:9]2[CH:10]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]1=2

参加物

反応物 3

HCID 996Phenol

HCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-

HCID 6451240Aluminum(III) Chloride

生成物 1

HCID 2687865,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol収率 32.1%

実験手順

27.5 g (0.2 mol) of anhydrous aluminum chloride were added by spatula to 250.0 g (2.65 mol) of phenol plus 414.5 g (2.27 mol) of 2,5-dichloro-2,5-dimethylhexane in 500 ml of petroleum ether at room temperature while stirring. After 48 hours, the reaction mixture was poured into ice-water and extracted with ether, and the organic phase was washed to neutrality with water, dried over sodium sulfate and evaporated under reduced pressure. Two recrystallizations of the residue from methanol yielded 148.7 g of the title compound of melting point 219°-220° C.