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

HRID 1466113Notes

Reaction equation

HRID 1466113 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

To a solution of 6-(1,3-dioxolan-2ylmethyl)-1H-isochromen-1-one (410 mg, 1.8 mmol) in dioxane (20 mL) was added HCl (20 ml, 3M), and then stirred for 16 hours. The reaction was extracted with ethyl acetate then separated. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to yield the title product. LC-MS (IE, m/z): 189 [M+1]+.

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-6973bd27dfa44dcfb8dd1af151a6fad7
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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