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

HRID 2092668Notes

Reaction equation

HRID 2092668 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-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[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

5

Reactant 3

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

Product 1

HCID 105606143-(4-Bromophenyl)propan-1-olYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 3-(4-bromophenyl)-propionic acid (3.0 g, [CAS Reg. No. 1643-30-7]) in diethyl ether (50 mL) was added lithium aluminium hydride (746 mg) in three portions. The mixture was then heated to reflux for 16 hours. The mixture was cooled to room temperature and saturated sodium sulfate solution (3 mL) was added dropwise over a period of 5 minutes. Stirring was continued for 30 minutes at RT. A white precipitation was obtained. The solid was filtered off, washed with diethyl ether and the filtrate was concentrated in vacuo to afford the title compound as a colorless liquid (2.62 g, 93%) that was used without further purification. MS (EI): 215.0 [MH+].

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 16 hours
  3. customA white precipitation
  4. customwas obtained
  5. filtrationThe solid was filtered off
  6. washwashed with diethyl ether
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-13ab6ec40fba4912a4e57083541c11ba
Source dataset
uspto-grants-2013_05
Patent number
US08440710B2

Reaction notes

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