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

HRID 1466115Notes

Reaction equation

HRID 1466115 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 RT over night, and then was warmed to 50° C. for 2 hrs to drive the reaction to completion. 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. LCMS: m/z 191 (M+1)+.

Workup

  1. temperaturewas warmed to 50° C. for 2 hrs
  2. customthe reaction to completion
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted again with ethyl acetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-e66af9a2442440e292a7429824fc4d2b
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

Loading…