Hydrochloric Acid → 3-(4-Bromophenoxy)propanoic acid

HRID 2096513

Reaction equation

HRID 2096513 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Br[CH2:12][CH2:13][C:14]([OH:16])=[O:15].Cl>>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 78084-BromophenolHCID 115533-Bromopropionic acidHCID 14798Sodium Hydroxide2×

Product 1

HCID 74720343-(4-Bromophenoxy)propanoic acidYield 61.2%

Conditions

Temperature
0 °C

Procedure

To a solution of aqueous NaOH (0.5 M, 0.2 mol) was slowly added 4-bromophenol (34.4 g, 0.2 mol) at room temperature. After heating to boiling, 3-bromopropanoic acid (30.60 g 0.2 mol) in aqueous NaOH (0.5M, 0.2 mol) was added dropwise to the mixture above. The resulting mixture was then refluxed for 2 h. The mixture was cooled to 0° C. and the pH of the mixture was adjusted to 6-7 with 0.5 N HCl. The resulting mixture was filtered to give a solid cake, which was washed with water and n-pentane and dried to give 3-(4-bromophenoxy)propanoic acid (30 g, 60%). 1H-NMR (CDCl3): 2.72 (m, 2H), 4.90 (s, 1H), 5.01 (d, 1H), 5.50 (s, 1H), 6.73 (m, 1H), 7.21-7.43 (m, 6H), 7.61 (m, 1H).

Workup

  1. customat room temperature
  2. additionwas added dropwise to the mixture above
  3. temperatureThe resulting mixture was then refluxed for 2 h
  4. filtrationThe resulting mixture was filtered
  5. customto give a solid cake, which
  6. washwas washed with water and n-pentane
  7. customdried

Sources & evidence

ORD record
ord-4af047a78ef5493cba32146021ebee64
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Linked notes

Loading…