HCID 13753192, compound → HCID 13753189, compound

HRID 1732159Notes

Reaction equation

HRID 1732159 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:28]=[CH:27][C:11]([O:12][C:13]2[CH:26]=[CH:25][C:16]([O:17][CH:18]([CH3:24])[C:19](OCC)=[O:20])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1>C(OCC)C>[F:7][C:8]1[CH:28]=[CH:27][C:11]([O:12][C:13]2[CH:26]=[CH:25][C:16]([O:17][CH:18]([CH3:24])[CH2:19][OH:20])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 13753192HCID 13753192, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13753189HCID 13753189, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1 g of lithium aluminium hydride is added to 20 ml of absolute diethyl ether and the solution in cooled by means of an ice-bath. While stirring, a solution of 5.8 g of ethyl 2-[p-(p-fluorophenoxy)phenoxy]-propionate in 50 ml of diethyl ether is added dropwise at such a rate that the temperature does not rise above 20° C. The mixture is subsequently allowed to stir at room temperature for 1.5 hours and then cautiously poured into 100 ml of ice-cold ammonium chloride solution. The mixture is extracted twice with diethyl ether, and the extracts are washed with semi-saturated and saturated sodium chloride solution, dried over anhydrous sodium sulfate and evaporated. The yellow oily residue is distilled in a bulb-tube at 140°-142° C./0.04 Torr to yield pure 2-[p-(p-fluorophenoxy)phenoxy]-propanol.

Workup

  1. temperaturethe solution in cooled by means of an ice-bath
  2. customdoes not rise above 20° C
  3. stirringto stir at room temperature for 1.5 hours
  4. extractionThe mixture is extracted twice with diethyl ether
  5. washthe extracts are washed with semi-saturated and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. distillationThe yellow oily residue is distilled in a bulb-tube at 140°-142° C./0.04 Torr

Sources & evidence

ORD record
ord-0bc4096b404043209e5fe6f23ff42e7b
Source dataset
uspto-grants-1986_11
Patent number
US04625048

Reaction notes

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