Hydrochloric Acid → 3-(2-Thenoyl)propionic acid

HRID 874985Notes

Reaction equation

HRID 874985 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:11])[O:10][C:8](=[O:9])[CH2:7][CH2:6]1.[S:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.Cl>C(Cl)Cl>[O:11]=[C:5]([C:13]1[S:12][CH:16]=[CH:15][CH:14]=1)[CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 8030ThiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 783853-(2-Thenoyl)propionic acidYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Anhydrous aluminium chloride (15.8 g, 0.12 mol) was added to a solution of succinic anhydride (11.9 g, 0.12 mol) in dry CH2Cl2 (50 MI) and the reaction mixture was cooled to 0° C. A solution of thiophene (10.0 g, 0.12 mol) in CH2Cl2 (50 MI) was then added dropwise maintaining the same temperature. The reaction mixture was allowed to warm up to room temperature and stirred for 8 h. The mixture was then cooled to 0° C. and the Ph was adjusted to ˜3 using 6N HCl. The organic product was extracted with CH2Cl2. The combined extracts were washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 5-10% MeOH in CH2Cl2), to get 4-oxo-4-(thiophen-2-yl)butanoic acid (8.3 g, yield 38%). 1H NMR (400 MHz, DMSO-d6) δ 12.18 (s, 1H), 8.00-7.98 (m, 2H), 7.26-7.23 (m, 1H), 3.21-3.18 (m, 2H), 2.58-2.55 (m, 2H). MS (ESI) m/z: Calculated for C8H8O3S: 184.02. found: 184.9 (M+H)+

Workup

  1. temperaturemaintaining the same temperature
  2. temperatureto warm up to room temperature
  3. temperatureThe mixture was then cooled to 0° C.
  4. extractionThe organic product was extracted with CH2Cl2
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluant 5-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-a069c1d6218f436c92a3a0a05a46e2ea
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

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