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

HRID 981001Notes

Reaction equation

HRID 981001 reaction equation
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:10]Cl.Cl[C:13]([CH3:21])([CH2:15][C:16](Cl)(C)[CH2:17][CH3:18])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH3:8][C:1]1[C:6]([OH:7])=[CH:5][C:4]2[C:13]([CH3:14])([CH3:21])[CH2:15][CH2:16][C:17]([CH3:18])([CH3:10])[C:3]=2[CH:2]=1

Participants

6

Reactant 4

HCID 335O-CresolHCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 12644949HCID 12644949, compound

Product 1

HCID 2266903,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-olYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Into a round bottom flask there are introduced 10.8 g (100 mmoles) of ortho cresol, 100 ml of dichloromethane (CH2Cl2) and 18.3 g (100 mmoles) of 2,4-dichloro-2,4-dimethylhexane. The reaction mixture is cooled to 5° C. and there are added, in small quantities, 6.6 g (50 mmoles) of aluminum chloride. The temperature is permitted to rise to 20° C. The reaction mixture is stirred for 2 hours and it is then poured into 200 ml of water. The organic phase is decanted, dried on magnesium sulfate (MgSO4) and the solvents are evaporated. The residue is recrystallized in 100 ml of hexane, yielding 20.3 g (93%) of 3-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol which melts at 122°-123° C.

Workup

  1. customto rise to 20° C
  2. customThe organic phase is decanted
  3. customdried on magnesium sulfate (MgSO4)
  4. customthe solvents are evaporated
  5. customThe residue is recrystallized in 100 ml of hexane

Sources & evidence

ORD record
ord-ffd138303cae48b6958df0ac8c9a66c8
Source dataset
uspto-grants-1991_02
Patent number
USRE033533

Reaction notes

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