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

HRID 498932Notes

Reaction equation

HRID 498932 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:14]([CH3:22])([CH2:16][CH2:17][C:18](Cl)([CH3:20])[CH3:19])[CH3:15]>ClCCl.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[C:5]2[C:14]([CH3:22])([CH3:15])[CH2:16][CH2:17][C:18]([CH3:20])([CH3:19])[C:6]=2[CH:7]=1

Participants

6

Reactant 3

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-olYield 68%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

60 g (347 mmol) of 3-bromophenol are dissolved in 600 mL of dichloromethane. This solution is added to a solution of 46 g (347 mmol) of aluminum chloride in 200 mL of dichloromethane. 127 g (694 mmol) of 2,5-dichloro-2,5-dimethylhexane are added in 10 g portions every 40 minutes. The medium is then stirred for 10 hours, after which it is poured onto ice and extracted with dichloromethane. The residue obtained is dissolved in ethyl ether and this organic phase is then washed with 1N sodium hydroxide solution, and then with water. The residue obtained is purified by chromatography (eluent:heptane and then 1/1 heptane/dichloromethane). A thick oil is obtained (67 g; yield=68%).

Workup

  1. additionafter which it is poured onto ice
  2. extractionextracted with dichloromethane
  3. customThe residue obtained
  4. washthis organic phase is then washed with 1N sodium hydroxide solution
  5. customThe residue obtained
  6. customis purified by chromatography (eluent
  7. customA thick oil is obtained (67 g; yield=68%)

Sources & evidence

ORD record
ord-646d7a05e92c4e77900110a21bfe85da
Source dataset
uspto-grants-2010_08
Patent number
US07767650B2

Reaction notes

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