Hydrochloric Acid → 3-Ethoxyoxan-4-one

HRID 1436757Notes

Reaction equation

HRID 1436757 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-d00e169bc8974358813251856888fdb3
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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