Hydrochloric Acid → 3-(4-Bromophenyl)propionic acid

HRID 1641043Notes

Reaction equation

HRID 1641043 reaction equation
CC1(C)[O:7][C:6](=[O:8])[CH2:5][C:4](=O)O1.[Br:11][C:12]1[CH:19]=[CH:18][C:15](C=O)=[CH:14][CH:13]=1.Cl>C(O)(=O)C.O>[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:4][CH2:5][C:6]([OH:7])=[O:8])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 707414-Bromobenzaldehyde

Product 1

HCID 27356093-(4-Bromophenyl)propionic acidYield 67%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2,2-dimethyl-[1,3]dioxane-4,6-dione (120 g, 0.84 mol) and 4-bromo-benzaldehyde (153.4 g, 0.84 mol) were dissolved in 300 mL of TEA and acetic acid. The reaction mixture was refluxed for overnight. At which point, the reaction mixture was diluted with water (4 L) and acidified with 6M HCl (1 L) until pH=2. The precipitated solid was filtered off and washed with diluted HCl, then dissolved in 5% NaHCO3 solution. The aqueous salt solution was washed with ether (4×500 mL), filtered and acidified with diluted HCl. Then filtered and dried under vacuum to provide 100 g (67%) of the desired product 3-(4-bromophenyl)propanoic acid (1A): 1H NMR (DMSO-d6, 400 MHz), 62.5 (m, 2H), 2.8 (m, 2H), 7.2 (m, 2H), 7.5 (m, 2H), 12.2 (s, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for overnight
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with diluted HCl
  4. dissolutiondissolved in 5% NaHCO3 solution
  5. washThe aqueous salt solution was washed with ether (4×500 mL)
  6. filtrationfiltered
  7. filtrationThen filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-f33cbea23fdb47f1bee8d3a06ff090f2
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

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