Hydrochloric Acid → (1-oxo-1H-isochromen-6-yl)acetaldehyde

HRID 2173152Notes

Reaction equation

HRID 2173152 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[O:12][CH:11]=[CH:10]2.Cl>O1CCOCC1>[O:17]=[C:13]1[C:14]2[C:9](=[CH:8][C:7]([CH2:6][CH:2]=[O:1])=[CH:16][CH:15]=2)[CH:10]=[CH:11][O:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 772306596-(1,3-Dioxolan-2-ylmethyl)isochromen-1-one

Product 1

HCID 77230658(1-oxo-1H-isochromen-6-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-(1,3-dioxolan-2ylmethyl)-1H-isochromen-1-one (410 mg, 1.77 mmol) was dissolved in dioxane (20 mL) and HCl (20 mL, 3M) was added then stirred for 16 hrs. The reaction was extracted with ethyl acetate then separated. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. to yield (1-oxo-1H-isochromen-6-yl)acetaldehyde LC-MS (IE, m/z): 189 [M+1]+; 1H-NMR (500 MHz, CDCl3) δ ppm 9.86 (s, 1H), 8.33 (d, J=8 Hz, 1H), 7.41 (d, J=8 Hz, 1H), 734(s, 2H), 6.52 (d, J=5.5 Hz, 1H), 3.89 (s, 2H).

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. customthen separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7dcf4645ca9e4800a371d68e1ceb608e
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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