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

HRID 1896555Notes

Reaction equation

HRID 1896555 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-3a9e44271f67462db54dd77b0436143a
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

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