Hydrochloric Acid → HCID 86079822, compound

HRID 2217161Notes

Reaction equation

HRID 2217161 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=1.Cl>C1COCC1>[CH:2]([CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=1)=[O:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 692226804-[2-(1,3-Dioxolan-2-yl)ethyl]benzamide

Product 1

HCID 86079822HCID 86079822, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(2-(1,3-dioxolan-2-yl)ethyl)benzamide (0.50 g, 2.26 mmol) in THF (22 mL) was added 1 N HCl solution (20 mL) at room temperature. The mixture was heated at 80? 90? for 1 h and cooled to room temperature. After saturation with NaCl, the reaction mixture was extracted repeatedly with CHCl3 (5×20 mL). The combined CHCl3 solution was dried (anhydrous Na2SO4), filtered, and evaporated under reduced pressure to give 0.40 g (98%) of 4-(2-formylethyl)benzamide as a solid which was used to the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 9.82 (t, 1H), 7.74 (m, 2H), 7.27 (m, 2H), 6.14 (br s, 1H), 6.03 (br s, 1 H), 3.01 (m, 2H), 2.81 (m, 2H).

Workup

  1. temperatureThe mixture was heated at 80
  2. extractionAfter saturation with NaCl, the reaction mixture was extracted repeatedly with CHCl3 (5×20 mL)
  3. dry with materialThe combined CHCl3 solution was dried (anhydrous Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-772a73f1577049db87333252a394bce4
Source dataset
uspto-grants-2008_08
Patent number
US07407958B2

Reaction notes

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