Sodium Hydroxide → 1-(2,6-Dichloro-3-fluorophenyl)ethan-1-ol

HRID 1627516Notes

Reaction equation

HRID 1627516 reaction equation
[CH3:1][C:2]([C:4]1[C:9]([Cl:10])=[C:8]([F:11])[CH:7]=[CH:6][C:5]=1[Cl:12])=[O:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[Cl:10][C:9]1[C:8]([F:11])=[CH:7][CH:6]=[C:5]([Cl:12])[C:4]=1[CH:2]([OH:3])[CH3:1]

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 24083Sulfuric acid magnesium salt (1:1)HCID 27339821-(2,6-Dichloro-3-fluorophenyl)ethanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 167700681-(2,6-Dichloro-3-fluorophenyl)ethan-1-olYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,6-Dichloro-3-fluoroacetophenone (15 g, 0.072 mol) was stirred in THF (150 mL, 0.5M) at 0° C. using an ice bath for 10 min. Lithium aluminum hydride (from Aldrich, 2.75 g, 0.072 mol) was slowly added. The reaction was stirred at ambient temperature for 3 h. The reaction was cooled in ice bath, and water (3 mL) was added drop wisely followed by adding 15% NaOH (3 mL) slowly. The mixture was stirred at ambient temperature for 30 min. 15% NaOH (9 mL), MgSO4 were added and the mixture filtered to remove solids. The solids were washed with THF (50 mL) and the filtrate was concentrated to give 1-(2,6-dichloro-3-fluoro-phenyl)-ethanol (14.8 gm, 95% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 1.45 (d, 3H), 5.42 (m, 2H), 7.32 (m, 1H), 7.42 (m, 1H).

Workup

  1. customfor 10 min
  2. temperatureThe reaction was cooled in ice bath
  3. stirringThe mixture was stirred at ambient temperature for 30 min
  4. filtrationthe mixture filtered
  5. customto remove solids
  6. washThe solids were washed with THF (50 mL)
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2898f82d6e4e44ceafc53b140e4778b2
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

Loading…