Sodium Hydroxide → 3-(4-Bromophenyl)propan-1-ol

HRID 1927641Notes

Reaction equation

HRID 1927641 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](O)=[O:17])=[CH:10][CH:9]=1.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C(OCC)C.C1COCC1.CCCCCC.O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:12][CH:13]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 27356093-(4-Bromophenyl)propionic acidHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a suspension of lithium aluminum hydride (2.39 g, 62.9 mmol) in diethyl ether (100 mL) at 0° C. was added 3-(4-bromophenyl)propionic acid (9.59 g, 41.9 mmol) in THF (100 mL). After stirring at rt for 2 h, the reaction mixture was cooled to 0° C. and H2O (2.5 mL), NaOH (15% aq., 2.5 mL), H2O (5 mL), Et2O (200 mL), hexane (50 ml), and anhydrous Na2SO4 were added sequentially. The suspension was stirred at it for 1 h and was filtered, and the filtrate was concentrated to afford 3-(4-bromophenyl)-propanol.

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. stirringThe suspension was stirred at it for 1 h
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b25b0dc8e1d74598a1d3d1a16533439b
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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