p-Toluenesulfonic acid → 6-Bromo-4-tert-butyl-1,1-dimethyl-1,2-dihydronaphthalene

HRID 2186416Notes

Reaction equation

HRID 2186416 reaction equation
[C:1]([C:5]1(O)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Br:15])[CH:13]=2)[C:8]([CH3:17])([CH3:16])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Br:15])[CH:13]=2)[C:8]([CH3:17])([CH3:16])[CH2:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 224561861-t-Butyl-1-hydroxy 4,4-dimethyl-7-bromo-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 158960196-Bromo-4-tert-butyl-1,1-dimethyl-1,2-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of the crude 1-t-butyl-1-hydroxy 4,4-dimethyl-7-bromo-1,2,3,4-tetrahydronaphthalene , MeOH (30 mL) and p-TSA (150 mg) were heated for 17 h at 70° C. Reaction mixture was cooled to ambient temperature and solid K2CO3 was added and the MeOH was removed by evaporation. The residue was diluted with ether. The ether layer was washed with water and brine and the ether was dried (MgSO4) and removed by evaporation. Purification by silica gel chromatography yielded 1.65 g (28%, in two steps) the title compound as a clear oil.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to ambient temperature
  3. customthe MeOH was removed by evaporation
  4. additionThe residue was diluted with ether
  5. washThe ether layer was washed with water and brine
  6. dry with materialthe ether was dried (MgSO4)
  7. customremoved by evaporation
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-f7ad123a9c144e03a4b103e9ebdcf77b
Source dataset
uspto-grants-2002_06
Patent number
US06403638B1

Reaction notes

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