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

HRID 591262Notes

Reaction equation

HRID 591262 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-].C(=O)([O-])O.[Na+]>O1CCCC1>[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 516892Sodium BicarbonateHCID 27356093-(4-Bromophenyl)propionic acidHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(4-bromophenyl)propionic acid (Aldrich) (12.25 g, 53.48 mmol) was dissolved in tetrahydrofuran (100 mL) and the solution was slowly added to lithium aluminum hydride (1.22 g, 32.09 mmol) in tetrahydrofuran (100 mL). The reaction was stirred for 3 h, then 150 mL 1 N aqueous sodium hydrogen carbonate was added, the mixture was extracted with ethyl acetate (3×150 mL) and the organic phases were dried over magnesium sulphate and concentrated in vacuo. The crude product was used without purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×150 mL)
  2. dry with materialthe organic phases were dried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was used without purification

Sources & evidence

ORD record
ord-492808e67fe348a3be8ed3d636114099
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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