Dichloromethane → {2-Chloro-6-[(diethylamino)methyl]phenyl}methanol

HRID 630258Notes

Reaction equation

HRID 630258 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:3]=1[C:4](OC)=[O:5].[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].ClCCl>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([CH2:14][CH3:15])[CH2:16][CH3:17])[C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 59589357Methyl 2-chloro-6-[(diethylamino)methyl]benzoate

Product 1

HCID 59589378{2-Chloro-6-[(diethylamino)methyl]phenyl}methanolYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To methyl 2-chloro-6-[(diethylamino)methyl]benzoate (3.97 g, 15.5 mmol) in anhydrous THF (100 mL) was added a solution of diisobutylaluminium hydride (1 M in toluene, 35 mL, 35 mmol). The reaction mixture was stirred at room temperature for 90 minutes. A Rochelle's salt solution (200 mL) and dichloromethane (200 mL) were added. The mixture was stirred at room temperature for 2 hours. The organic layer was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording {2-chloro-6-[(diethylamino)methyl]phenyl}methanol (3.0 mg, 85% yield), which was used without further purification.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. customThe organic layer was recovered
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-473e18fb81314d38a2172f61f8768b67
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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