Hydrochloric Acid → 3-Ethoxyoxan-4-one

HRID 1044557Notes

Reaction equation

HRID 1044557 reaction equation
[CH2:1]([O:3][CH:4]1[C:9](OC)([O:10]C)[CH2:8][CH2:7][O:6][CH2:5]1)[CH3:2].Cl>C1COCC1.O.CCOC(C)=O>[CH2:1]([O:3][CH:4]1[C:9](=[O:10])[CH2:8][CH2:7][O:6][CH2:5]1)[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 579387433-Ethoxy-4,4-dimethoxytetrahydro-2H-pyran

Product 1

HCID 235335993-Ethoxyoxan-4-oneYield 97.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 3-ethoxy-4,4-dimethoxytetrahydro-2H-pyran (2.1 g, 11 mmol) in THF/water (50 mL/10 mL) was added concentrated HCl (6 mL). After being stirred at room temperature for 1 h, the mixture was diluted with EtOAc. The organic layer was separated and the aqueous layer was extracted with ether five times. The combined organic layers were dried over MgSO4, filtered and concentrated to give 1.55 g (97%) of the desired product 1H NMR (CDCl3) δ 4.30-3.50 (7H, m), 2.62-2.57 (2H, m), 1.30-1.20 (3H, t, J=5 Hz).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ether five times
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5985b3823d03404e800247705be0f455
Source dataset
uspto-grants-2013_10
Patent number
US08563582B2

Reaction notes

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