Hydrochloric Acid → HCID 59120745, compound

HRID 1430598Notes

Reaction equation

HRID 1430598 reaction equation
[O:1]=[C:2]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)[CH:3]([C:9]1[CH:10]=[C:11]([CH3:15])[CH:12]=[CH:13][CH:14]=1)C(OCC)=O.Cl>O>[C:11]1([CH3:15])[CH:12]=[CH:13][CH:14]=[C:9]([CH2:3][C:2]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)=[O:1])[CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67434527HCID 67434527, compound

Product 1

HCID 59120745HCID 59120745, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ethyl 3-oxo-2-m-tolyl-3-p-tolylpropanoate (2.213 g, 7.47 mmol) was added aqueous HCl solution (8.96 mL, 112 mmol). The reaction was heated to reflux overnight. The reaction was cooled to room temperature, the mixture was diluted with water and extracted with EtOAc three times. The combined extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a white solid (1.174 g). 1H NMR (400 M Hz, CDCl3) δ ppm 2.31-2.32 (m, 3H), 2.40 (s, 3H), 4.21 (s, 2H), 7.00-7.09 (m, 3H), 7.20 (t, J=7.45 Hz, 1H), 7.22-7.27 (m, 2H), 7.91 (d, J=8.34 Hz, 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. extractionextracted with EtOAc three times
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6d6fa8db98f942c2958a43d1a8ea8f84
Source dataset
uspto-grants-2015_01
Patent number
US08940891B2

Reaction notes

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