Acetone → 4-(4-Bromophenyl)butan-1-ol

HRID 70567Notes

Reaction equation

HRID 70567 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])=[CH:10][CH:9]=1.CC(C)=O.O>O1CCCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 2527324-(4-Bromophenyl)butyric AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 282961564-(4-Bromophenyl)butan-1-olYield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (759 mg) was added to a solution of 4-(4-bromophenyl)butyric acid (3.12 g) in tetrahydrofuran (90 mL) under ice-cooling, and the mixture was stirred under ice-cooling for one hour. Acetone and water were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1→10:1→7:1 5:1) to give 4-(4-bromophenyl)butan-1-ol (2.29 g, quant.).

Workup

  1. temperaturecooling
  2. temperaturecooling for one hour
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1→10:1→7:1 5:1)

Sources & evidence

ORD record
ord-f7b406bef5cd4f75aa91fc8b4854d879
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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