Boron tribromide → 4-(4-Hydroxyphenyl)butanoic acid

HRID 1250923Notes

Reaction equation

HRID 1250923 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 782804-(4-Methoxyphenyl)butyric acidHCID 516892Sodium Bicarbonate

Product 1

HCID 2799834-(4-Hydroxyphenyl)butanoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.00 g (5.15 mmol) of 4-(4-methoxyphenyl)butyric acid in 100 mL of dichloromethane at 0° C. was added 15.5 mL (15.5 mmol) of boron tribromide and the reaction was then allowed to warm to room temperature and stirred for 2 h. The reaction mixture was then poured into 200 mL of saturated sodium bicarbonate solution and the organic layer was separated. The aqueous layer was acidified with concentrated HCl solution and then extracted with dichloromethane. The combined organics were dried over MgSO4, filtered and concentrated in vacuo to provide 0.696 g of impure 4-(4-hydroxyphenyl)butyric acid.

Workup

  1. customthe organic layer was separated
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53ba6ba36bc8486b9504fd2e3401c918
Source dataset
uspto-grants-2002_01
Patent number
US06340691B1

Reaction notes

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