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

HRID 425917Notes

Reaction equation

HRID 425917 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-ee8ce99ba8a54e7c9a651a9548465230
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

Loading…