Triphenylcarbinol → 2-Chloro-6-methylnaphthalene

HRID 1432855Notes

Reaction equation

HRID 1432855 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7]([CH3:13])(O)[CH2:6][CH2:5]2.C(O)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 6457TriphenylcarbinolHCID 538109156-Chloro-2-methyl-1,2,3,4-tetrahydronaphthalene-2-ol

Product 1

HCID 187276682-Chloro-6-methylnaphthalene

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 6-chloro-2-methyl-1,2,3,4-tetrahydronaphthalene-2-ol (11.3 g, 57.5 mmol) and Ph3COH (16.5 g, 63 mmol) in 80 mL of TFA is stirred for 2.5 days. After this time, the solution is concentrated to dryness. The residue is dissolved in CH2Cl2. The organic layer is washed with H2O, saturated NaHCO3, and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with hexanes. The title compound is obtained as a white solid (4.05 g, 22.9 mmol). 1H NMR (CDCl3, 300 MHz) δ7.78 (s, 1H), 7.69 (m, 2H), 7.58 (s, 1H), 7.50 (m, 2H), 2.49 (s, 3H).

Workup

  1. concentrationAfter this time, the solution is concentrated to dryness
  2. dissolutionThe residue is dissolved in CH2Cl2
  3. washThe organic layer is washed with H2O, saturated NaHCO3, and saturated NaCl
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by column chromatography
  8. washeluting with hexanes

Sources & evidence

ORD record
ord-a5e15fc7d2714a689d1fbd7a538a9beb
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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