Water → 2-(4-Chlorophenyl)-1-propanol

HRID 1440996Notes

Reaction equation

HRID 1440996 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15](O)=[O:16])=[CH:10][CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([CH3:18])[CH2:15][OH:16])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 102525DL-2-(4-chlorophenyl)propanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 5870302-(4-Chlorophenyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3.8 g (0.10 mole) of lithium aluminum hydride in 50 mL of tetrahydrofuran is added dropwise a solution of 18.4 g (0.10 mole) of 2-(4-chlorophenyl)propionic acid in 200 mL of tetrahydrofuran. This reaction mixture is allowed to stir at ambient temperature for a period of approximately 16 hours after which it is cooled by an ice/water bath. To the cooled reaction mixture are added in sequence 4 mL of water, 4 mL of a 10% aqueous solution of sodium hydroxide, and 12 mL of water. The mixture is then filtered, and the filter cake is washed with diethyl ether. The diethyl ether wash is combined with the filtrate, and the combination is dried over anhydrous magnesium sulfate. The solvents are then evaporated under reduced pressure, leaving 2-(4-chlorophenyl)propanol as a residue.

Workup

  1. temperatureis cooled by an ice/water bath
  2. customTo the cooled reaction mixture
  3. filtrationThe mixture is then filtered
  4. washthe filter cake is washed with diethyl ether
  5. washThe diethyl ether wash
  6. dry with materialthe combination is dried over anhydrous magnesium sulfate
  7. customThe solvents are then evaporated under reduced pressure

Sources & evidence

ORD record
ord-f3e37a436194445bb7669be98cb3a3f7
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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