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

HRID 2240991Notes

Reaction equation

HRID 2240991 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][C:11](O)=[O:12])[CH:5]=[CH:6][CH:7]=1.[H]1[BH2][H][BH2]1.C1COCC1.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 183294554-(3-Bromophenyl)butanoic acid

Product 1

HCID 218954894-(3-Bromophenyl)butan-1-olYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cold (0° C.) solution of 4-(3-bromophenyl)butyric acid (2.85 g, 11.7 mmol) in THF was treated slowly with a solution of B2H6-THF (35 mL), stirred at room temperature for 18 hours, poured into ice/water, basified with 2.5 N NaOH to pH=11 and extracted with CH2Cl2. The extracts were combined, washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the resultant residue by column chromatography using hexanes/CH2Cl2/MeOH (4/4.5/0.5) as the eluting solvent afforded 4-(3-bromophenyl)butan-1-ol as a colorless oil (1.9 g, 70% yield.

Workup

  1. extractionextracted with CH2Cl2
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the resultant residue by column chromatography

Sources & evidence

ORD record
ord-55f91dedc70a4123856a6be6d8ba5264
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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