2-Chloroethanol → (4-Fluorophenyl)(4-(2-hydroxyethoxy)phenyl)methanone

HRID 240210

Reaction equation

HRID 240210 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.Cl[CH2:18][CH2:19][OH:20].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>CN(C)C=O.C(OCC)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:18][CH2:19][OH:20])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 342-ChloroethanolHCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1176664-Fluoro-4'-hydroxybenzophenone

Product 1

HCID 67170561(4-Fluorophenyl)(4-(2-hydroxyethoxy)phenyl)methanoneYield 99.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an oven-dried flask placed under a nitrogen atmosphere, 4-fluorophenyl-4-hydroxyphenyl methanone (100 g), 2-chloroethanol (75 g), potassium carbonate (134 g) and potassium iodide (11.5 g) were stirred in anhydrous dimethylformamide (400 mL) using a mechanical stirrer. The reaction mixture was heated to reflux for 4 hours. It was cooled to room temperature and then poured into a beaker containing deionized water (1 L) and ice. Concentrated hydrochloric acid was added while stirring vigorously until the pH reached 3. The mixture was transferred to a separatory funnel and then extracted with chloroform (2×600 mL). The organic layers were combined and washed with a saturated aqueous solution of sodium bicarbonate (750 mL), dried over sodium sulfate and concentrated by rotary evaporation to yield a solid. The solid was slurried in a minimal amount of a solution of 10% ethyl acetate/90% hexanes and collected by vacuum filtration. 120 grams of 4-fluorophenyl-4-(2-hydroxyethoxy)phenyl methanone was isolated.

Workup

  1. customIn an oven-dried flask placed under a nitrogen atmosphere
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 4 hours
  4. additionpoured into a beaker
  5. customThe mixture was transferred to a separatory funnel
  6. extractionextracted with chloroform (2×600 mL)
  7. washwashed with a saturated aqueous solution of sodium bicarbonate (750 mL)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated by rotary evaporation
  10. customto yield a solid
  11. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-54a2c352c4034dd19e6de31131a4eba9
Source dataset
uspto-grants-2014_02
Patent number
US08647538B2

Linked notes

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