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

HRID 1614881Notes

Reaction equation

HRID 1614881 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.ClCCl.Cl[C:16]([CH3:24])([CH2:18][CH2:19][C:20](Cl)([CH3:22])[CH3:21])[CH3:17]>O>[OH:11][C:5]1[CH:10]=[CH:9][C:8]2[C:20]([CH3:22])([CH3:21])[CH2:19][CH2:18][C:16]([CH3:24])([CH3:17])[C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 6344DichloromethaneHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride3×

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The synthesis process is as set forth in the chemical reaction formula below. The AlCl3 in the reaction path stands for aluminum chloride. Into phenol (1.02 g, 10.8 mmol) were added anhydrous dichloromethane (5 mL), aluminum chloride (144 mg, 1.08 mmol), and 2,5-dichloro-2,5-dimethylhexane (2.18 g, 11.9 mmol) followed by stirring at room temperature for 19 hours. The reaction solution was poured into cold water and extracted by ethyl acetate. The organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by recrystallization in a solvent of hexane. The yield was 1.83 g (83%).

Workup

  1. extractionextracted by ethyl acetate
  2. washThe organic layer was washed by water
  3. dry with materiala saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by recrystallization in a solvent of hexane

Sources & evidence

ORD record
ord-5882c151337f4c049761ccbd9576fef9
Source dataset
uspto-grants-2014_07
Patent number
US08765719B2

Reaction notes

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