Water → 16014-71-4

HRID 1648863Notes

Reaction equation

HRID 1648863 reaction equation
[C:1]1([CH:7]([CH2:13][CH:14]=[CH2:15])[C:8](OCC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[C:1]1([CH:7]([CH2:13][CH:14]=[CH2:15])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 13005250HCID 13005250, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 57839416014-71-4Yield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.0 g of ethyl 2-phenyl-4-pentenoate in 10 ml of tetrahydrofuran is added dropwise to a stirred suspension of 2.0 g of lithium aluminum hydride in 40 ml of tetrahydrofuran at room temperature. The resulting mixture is stirred at 40°-45° C. for 2 hours. Under ice-cooling, water (10 ml) is added dropwise to the reaction mixture in order to decompose the unreacted lithium aluminum hydride. The mixture is poured into 200 ml of ice-cold water and extracted with 200 ml of benzene. The extract is washed with water and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by column chromatography on silica gel with chloroform eluate to give 2.4 g of 2-phenyl-4-penten-1-ol as colorless oil.

Workup

  1. temperatureUnder ice-cooling
  2. extractionextracted with 200 ml of benzene
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel with chloroform eluate

Sources & evidence

ORD record
ord-07203f8bab544fbfae37864511195222
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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