O-Cresol → 3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1275614Notes

Reaction equation

HRID 1275614 reaction equation
Cl[C:2]([CH3:10])([CH2:4][CH2:5][C:6](Cl)([CH3:8])[CH3:7])[CH3:3].[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH3:11][C:12]1[C:13]([OH:18])=[CH:14][C:15]2[C:2]([CH3:10])([CH3:3])[CH2:4][CH2:5][C:6]([CH3:8])([CH3:7])[C:16]=2[CH:17]=1

Participants

5

Reactant 3

HCID 335O-CresolHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 2266903,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50.8 g (0.27 mol) of 2,5-dichloro-2,5-dimethylhexane, 30 g (0.27 mol) of 2-methylphenol and 500 ml of dichloromethane were introduced into a three-necked flask. 14.8 g (0.11 mol) of aluminum chloride were added in small amounts at 0° C. and the entire contents were stirred at room temperature for twelve hours. The reaction medium was poured into ice-cold water, extracted with dichloromethane, the organic phase decanted off, washed with sodium bicarbonate, dried over magnesium sulfate and evaporated.

Workup

  1. additionThe reaction medium was poured into ice-cold water
  2. extractionextracted with dichloromethane
  3. customthe organic phase decanted off
  4. washwashed with sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-a03815e5314a4830932da090fc20d51c
Source dataset
uspto-grants-2000_12
Patent number
US06162815

Reaction notes

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