Hydrochloric Acid → HCID 58043122, compound

HRID 1035214Notes

Reaction equation

HRID 1035214 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[C:9]([O:12]C2CCCCO2)[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].Cl>C(O)C>[OH:12][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[C:3]([O:2][CH3:1])[C:10]=1[CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 107531772-Methoxy-3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde

Product 1

HCID 58043122HCID 58043122, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methoxy-3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde—for preparation see e.g. Journal of Medicinal Chemistry, 41, 4819-4832 (1998)—(2.10 g, 8.4 mmol) was dissolved in ethanol (40 mL) and then HCl (2M, 40 mL) was added. After 20 minutes the solution was concentrated under reduced pressure. The aqueous residue was extracted twice with EtOAc and the combined organic solutions were washed with brine. The solution was dried over Na2SO4 and the solvent was removed by evaporation. The product was washed with petroleum-ether. There was obtained 1.0 g (72%) of 52A as a solid. 1H NMR (500 MHz, CDCl3): δ 2.05 (s, 3H), 3.78 (s, 3H), 6.74 (d, 1H), 7.49 (d, 1H), 10.05 (s, 1H).

Workup

  1. concentrationAfter 20 minutes the solution was concentrated under reduced pressure
  2. extractionThe aqueous residue was extracted twice with EtOAc
  3. washthe combined organic solutions were washed with brine
  4. dry with materialThe solution was dried over Na2SO4
  5. customthe solvent was removed by evaporation
  6. washThe product was washed with petroleum-ether

Sources & evidence

ORD record
ord-f0adf8ecca024ebea9c7bbd4238d8e18
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

Loading…