Dichloromethane → 3-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-ol

HRID 1871555Notes

Reaction equation

HRID 1871555 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].ClCCl.[Br:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.Cl[C:17]([CH3:25])([CH2:19][CH2:20][C:21](Cl)([CH3:23])[CH3:22])[CH3:18]>O>[Br:8][C:9]1[CH:10]=[C:11]([OH:15])[C:12]2[C:17]([CH3:25])([CH3:18])[CH2:19][CH2:20][C:21]([CH3:23])([CH3:22])[C:13]=2[CH:14]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 115633-BromophenolHCID 80360Hexane, 2,5-dichloro-2,5-dimethyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 223454653-Bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

13.40 g (100.0 mmol) of aluminium chloride and 100 ml of dichloromethane are introduced into a three-necked flask under an argon atmosphere. A solution composed of 34.60 g (199.0 mmol) of 3-bromophenol, 89.00 g (486.0 mmol) of 2,5-dichloro-2,5-dimethylhexane and 300 ml of dichloromethane is added dropwise. The reaction mixture is stirred for sixteen hours at room temperature. The reaction mixture is poured into water and extracted with dichloromethane, the extract is washed with water and the organic phase is separated by settling, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column eluted with a mixture composed of 80% heptane and 20% dichloromethane. After evaporating the solvents, 30.00 g (53%) of the expected compound are collected in the form of white crystals with a melting point of 93° C.

Workup

  1. additionis added dropwise
  2. extractionextracted with dichloromethane
  3. washthe extract is washed with water
  4. customthe organic phase is separated
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a silica column
  9. washeluted with a mixture
  10. customAfter evaporating the solvents, 30.00 g (53%) of the expected compound
  11. customare collected in the form of white crystals with a melting point of 93° C.

Sources & evidence

ORD record
ord-143b0b77be0c46a695e6d521bb20482e
Source dataset
uspto-grants-2000_08
Patent number
US06103762

Reaction notes

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