6-Chloro-2-tetralone → 6-Chloro-2-methyl-1,2,3,4-tetrahydronaphthalene-2-ol

HRID 1432854Notes

Reaction equation

HRID 1432854 reaction equation
[CH3:1][Mg+].[Br-].[Cl:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C:10](=[O:15])[CH2:9][CH2:8]2>C(Cl)Cl.O.Cl[Ti](Cl)(Cl)Cl>[Cl:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C:10]([CH3:1])([OH:15])[CH2:9][CH2:8]2

Participants

6

Reactant 2

HCID 44561396-Chloro-2-tetraloneHCID 178418689HCID 178418689, compound

Product 1

HCID 538109156-Chloro-2-methyl-1,2,3,4-tetrahydronaphthalene-2-ol

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of TiCl4 (95 mL, 1M in toluene) at −45° C. is added a solution of CH3MgBr (4.2 mL 3M in THF). The solution is stirred for 20 minutes. After this time, 6-chloro-3,4-dihydro-1H-naphthalene-2-one (11.3 g, 63 mmol) in 80 mL of CH2Cl2 is added dropwise over 15 minutes. The reaction is stirred for an additional 15 min at −45° C. The solution is warmed to 0° C. After 2 h, the solution is diluted with H2O and CH2Cl2. The organic layer is dried over MgSO4, filtered and concentrated. The title compound is obtained as an oil (11.3 g, 57.5 mmol). 1H NMR (CDCl3, 300 MHz) δ7.10 (m, 2H), 6.97 (m, 1H), 3.02 (m, 2H), 2.80 (s, 3H), 1.85 (m, 2H), 1.80 (m, 2H).

Workup

  1. stirringThe reaction is stirred for an additional 15 min at −45° C
  2. waitAfter 2 h
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fc812cd494c046c4bcda191920a4bb10
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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