Sulfuric Acid → 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

HRID 24566

Reaction equation

HRID 24566 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]([CH3:14])(O)[CH3:12])[CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:11]([CH3:14])([CH3:12])[CH2:10][CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 225715955-(3-Bromophenyl)-2-methylpentan-2-ol2×

Product 1

HCID 105860636-Bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.0 g (58.3 mmol) of 5-(3-bromophenyl)-2-methylpentan-2-ol (Compound E) was cooled to 0° C. and then 2.8 ml of conc. H2SO4 was added. The mixture was stirred for 2.5 hours, diluted with water (20 ml) and extracted with Et2O (3×40 ml). The combined organic layers were washed with water, sat. aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. Purification by Kugelrohr distillation gave the title compound as a colorless oil.

Workup

  1. extractionextracted with Et2O (3×40 ml)
  2. washThe combined organic layers were washed with water, sat. aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. distillationby Kugelrohr distillation

Sources & evidence

ORD record
ord-121fda83a02d475a9abaa17eaf5c6112
Source dataset
uspto-grants-2005_02
Patent number
US06855832B2

Linked notes

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