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

HRID 1816423Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2,5-dichloro-2,5-dimethyl-hexane (Intermediate 1, 97 g, 0.53 mol) and phenol (50 g, 0.53 mol) in CHCl3 (500 mL) at 0° C. was added AlCl3 (71 g, 0.54 mmol) portionwise. After stirring for 2 h at 0° C., the mixture was poured onto ice and was extracted with Et2O. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. Recrystallization of the resulting solid from Et2O-hexane (1:1) gave the title compound as off-white crystals (95.7 g, 89%).

Workup

additionthe mixture was poured onto ice
extractionwas extracted with Et2O
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customRecrystallization of the resulting solid from Et2O-hexane (1:1)

Sources & evidence

ORD record: ord-d90484f25a20486489129bc3a8102765
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884820B2

Reaction notes

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