Hydrochloric Acid → HCID 23498951, compound

HRID 1836869Notes

Reaction equation

HRID 1836869 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:12]([CH3:20])([CH2:14][CH2:15][C:16](Cl)([CH3:18])[CH3:17])[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl.O>[OH:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][C:4]2[C:16]([CH3:18])([CH3:17])[CH2:15][CH2:14][C:12]([CH3:20])([CH3:13])[C:3]=2[CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31234BenzenepropanolHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 23498951HCID 23498951, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 14 g (103 mmol) of 3-phenyl-1-propanol and 18.2 g (123 mmol) of 2,5-dichloro-2,5-dimethylhexane in 100 mL of dichloromethane was added 15 g (113 mmol) of aluminum chloride. After the addition of aluminum chloride was complete, the reaction was heated to reflux. After 16 hours, the reaction mixture was cooled to room temperature and 100 mL of water was added, followed by 100 mL of 1N HCl. The reaction mixture was stirred for 2 hours, filtered through a Celite pad and the layers were separated. The aqueous layer was extracted with diethyl ether and the combined organic fractions were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (30% ethyl acetate/hexane) to afford 13.45 g (53%) of 2-(3-hydroxypropyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene.

Workup

  1. temperaturethe reaction was heated to reflux
  2. filtrationfiltered through a Celite pad
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with diethyl ether
  5. washthe combined organic fractions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8d5ab37936cc46739eeff222ecaf04ad
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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