Hydrochloric Acid → (3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl)acetaldehyde

HRID 2173143Notes

Reaction equation

HRID 2173143 reaction equation
Cl.[O:2]1CCO[CH:3]1[CH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[O:13][CH:12]([CH3:19])[CH2:11]2>O1CCOCC1>[CH3:19][CH:12]1[CH2:11][C:10]2[C:15](=[CH:16][CH:17]=[C:8]([CH2:7][CH:3]=[O:2])[CH:9]=2)[C:14](=[O:18])[O:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 675173636-(1,3-dioxolan-2-ylmethyl)-3-methyl-3,4-dihydro-1H-isochromen-1-one

Product 1

HCID 77230694(3-methyl-1-oxo-3,4-dihydro-1H-isochromen-6-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1:1 solution of dioxane:3N HCl was added to a flask containing of 99 mg (0.49 mmol) of 6-(1,3-dioxolan-2-ylmethyl)-3-methyl-3,4-dihydro-1H-isochromen-1-one; the reaction was then stirred at room temp overnight. The crude reaction mixture was then partitioned between water and DCM. The organic layer was washed with saturated sodium bicarbonate solution, followed by brine. The organic layer was then dried with magnesium sulfate, filtered and concentrated.

Workup

  1. customThe crude reaction mixture
  2. customwas then partitioned between water and DCM
  3. washThe organic layer was washed with saturated sodium bicarbonate solution
  4. dry with materialThe organic layer was then dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d19cd6e6036148a98b9ff0a9fcaceced
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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