Aluminium lithium hydride → HCID 22009710, compound

HRID 322305Notes

Reaction equation

HRID 322305 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][C:18](O)=[O:19])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22009765HCID 22009765, compound

Product 1

HCID 22009710HCID 22009710, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(3-benzyloxyphenyl)butyric acid (22.0 g) in tetrahydrofuran (150 ml) was added dropwise to a suspension of lithium aluminum hydride (6.18 g) in tetrahydrofuran (150 ml) at 0° C. and then stirred for one hour at room temperature. The reaction mixture was quenched with H2O, acidified with 1N-hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with 1N-hydrochloric acid, saturated aqueous sodium bicarbonate and water, dried (MgSO4), and concentrated under reduced pressure to give 4-(3-benzyloxyphenyl)butanol (20.5 g, 99%). Oily substance.

Workup

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with 1N-hydrochloric acid, saturated aqueous sodium bicarbonate and water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e828c6dfdd7f4d1680ad64a5457ac9dc
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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