Hydrochloric Acid → 2-(1-Oxoisochroman-6-yl)acetaldehyde

HRID 2281314Notes

Reaction equation

HRID 2281314 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][CH2:11][CH2:10]2.Cl.C(OCC)(=O)C>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)[CH2:10][CH2:11][O:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 675173746-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydroisochromen-1-one

Product 1

HCID 772306602-(1-Oxoisochroman-6-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-1H-isochromen-1-one (4.42 g, 18.9 mmol) was dissolved in dioxane (25 mL) and treated with 3 M HCl (40 mL). The reaction mixture was stirred at room temperature over night, then was warmed to 50° C. for 2 hours to drive the reaction to completion (however this led to increased side product production based on LCMS). Ethyl acetate was added and the layers were separated. The aqueous layer was extracted again with ethyl acetate, and the combined organic layers were washed with brine and dried over MgSO4 to afford the title compound.

Workup

  1. temperaturewas warmed to 50° C. for 2 hours
  2. customthe reaction to completion (however
  3. temperatureto increased side product production
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted again with ethyl acetate
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-c2662da7f5204f64bfe0430a13e24fd7
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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