3-(4-Bromophenyl)propionic acid → 3-(4-Bromophenyl)propan-1-ol

HRID 1662845Notes

Reaction equation

HRID 1662845 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 27356093-(4-Bromophenyl)propionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 105606143-(4-Bromophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(4-bromo-phenyl)-propionic acid (4.0 g, 18 mmol) in THF (30 mL) at 0° C. under the argon atmosphere was added LiAlH4 (1.0 M in THF; 14 mL, 14 mmol). After the addition, the ice-bath was removed and the mixture refluxed for 18 h. After cooling to room temperature, the reaction was quenched with 1 M HCl and the mixture extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and the crude product used in the next step without further purification.

Workup

  1. additionAfter the addition
  2. customthe ice-bath was removed
  3. temperaturethe mixture refluxed for 18 h
  4. customthe reaction was quenched with 1 M HCl
  5. extractionthe mixture extracted with ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customthe crude product used in the next step without further purification

Sources & evidence

ORD record
ord-7bfdf2391f214c3c9f65169fc0a92927
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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