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O-Cresol → 3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro2-naphthol

HRID 2351848
Notes
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Reaction equation

HRID 2351848 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-tetrahydro2-naphtholYield 93%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

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-7baa4a59e4ed4b96bea075b9720d1566
Source dataset
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04874747

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes