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

HRID 1384161Notes

Reaction equation

HRID 1384161 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 are introduced into a three-necked flask. 14.8 g (0.11 mol) of aluminium chloride are added portionwise, at 0° C., and the mixture is stirred at room temperature for twelve hours. The reaction medium is poured into ice-cold water, the mixture is extracted with dichloromethane and the organic phase is separated out after settling has taken place, washed with bicarbonate solution, dried over magnesium sulphate and evaporated. The residue obtained is triturated in hexane and filtered off and, after drying, 54.4 g (90%) of the expected phenol, with a melting point of 125-6° C., are collected.

Workup

  1. additionThe reaction medium is poured into ice-cold water
  2. extractionthe mixture is extracted with dichloromethane
  3. customthe organic phase is separated out after settling
  4. washwashed with bicarbonate solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis triturated in hexane
  9. filtrationfiltered off
  10. customafter drying
  11. custom54.4 g (90%) of the expected phenol, with a melting point of 125-6° C., are collected

Sources & evidence

ORD record
ord-2d35c697c07d4d3fb9331b577bdce734
Source dataset
uspto-grants-2001_07
Patent number
US06258775B1

Reaction notes

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