Water → 1-Phenyl-1,4-butanediol

HRID 260180Notes

Reaction equation

HRID 260180 reaction equation
[C:1]([CH2:9][CH2:10][C:11](O)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[C:2]1([CH:1]([OH:8])[CH2:9][CH2:10][CH2:11][OH:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 728713-Benzoylpropionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2638511-Phenyl-1,4-butanediolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Benzoylpropionic acid 11a dissolved in THF was reacted with LiAlH4 according to the general procedure. The following workup procedure was used: H2O was added and THF was evaporated. Diethylether and HCl (2M) was added. The aqueous layer was extracted with diethylether and the combined organic layers were washed with H2O, aqueous NaHCO3 (saturated) and H2O. Drying (MgSO4), filtration and evaporation gave 80% yield of 6a. 1H-NMR: 7.35-7.22 (m, 5H, Ar--H); 4.70 (t, 1H, CH--OH); 3.64 (t, 2H, CH2OH); 3.10 (brs, 1H, CH--OH); 2.60 (brs, 1H, CH2 --OH); 1.84 (q, 2H, CH2 --CHOH); 1.72-1.61 (m, 2H, CH2CH2OH).

Workup

  1. customTHF was evaporated
  2. additionDiethylether and HCl (2M) was added
  3. extractionThe aqueous layer was extracted with diethylether
  4. washthe combined organic layers were washed with H2O, aqueous NaHCO3 (saturated) and H2O
  5. customDrying
  6. filtration(MgSO4), filtration and evaporation

Sources & evidence

ORD record
ord-c29d0ecce3d941419947640350b2f4f2
Source dataset
uspto-grants-1996_06
Patent number
US05525736

Reaction notes

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