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

HRID 1265249Notes

Reaction equation

HRID 1265249 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[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]>ClCCl>[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

Participants

5

Reactant 3

HCID 996PhenolHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 2687865,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-olYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
32.5 °C

Procedure

Aluminum trichloride (25 g, 0.18 mol) was added portions to a solution of phenol (49.5 g, 0.52 mol) and 2,5-dichloro-2,5-dimethylhexane (101.0 g, 0.55 mol) in dichloromethane (700 mL). The reaction mixture was allowed to stir at 25-40° C. for 2 h, then the dark red mixture was poured onto ice water. Aqueous work up (EtOAc extraction) gave 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-ol 84.8 g (80%) as a white solid, which was recrystallized from hexane to give the product as colorless needles: 1H NMR (400 MHz, CDCl3) δ 7.17 (d, 1H, ArH), 6.78 (d, 1H, ArH), 6.62 (dd, 1H, ArH), 4.55 (s, 1H, OH), 1.65 (s, 4H, 2CH2), 1.25 (s, 12H, 4CH3).

Workup

  1. additionthe dark red mixture was poured onto ice water
  2. extractionAqueous work up (EtOAc extraction)

Sources & evidence

ORD record
ord-cd8984879219426da6576d23173d5fa3
Source dataset
uspto-grants-2003_04
Patent number
US06545049B1

Reaction notes

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