Boron tribromide → 5,5-DIMETHYL-5,6,7,8-TETRAHYDRONAPHTHALEN-2-OL

HRID 1350829Notes

Reaction equation

HRID 1350829 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][CH2:6]2.B(Br)(Br)Br>C(Cl)Cl>[CH3:13][C:9]1([CH3:14])[CH2:8][CH2:7][CH2:6][C:5]2[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11][C:10]1=2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 103525226-Methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 202877025,5-DIMETHYL-5,6,7,8-TETRAHYDRONAPHTHALEN-2-OLYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a methylene chloride (10 ml) solution of 6-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (Tetrahedron, 1994, 50, 3297) (2.28 g, 12.0 mmol) was added methylene chloride solution of boron tribromide (1M, 24 mL, 24.0 mmol) at 0° C. The mixture was stirred at 0° C. for 2 hours. The reaction mixture was then quenched with methanol and then the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with ethyl acetate/hexane=⅓ to furnish 2.0 g (96% yield) of the title compound as a white solid.

Workup

  1. customThe reaction mixture was then quenched with methanol
  2. customthe solvent was removed under reduced pressure
  3. customto give a residue, which
  4. washeluted with ethyl acetate/hexane=⅓

Sources & evidence

ORD record
ord-f136bb9048af4484b938118f14d052c8
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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