Hydrochloric Acid → 3-Methoxyoxan-4-one

HRID 1436749Notes

Reaction equation

HRID 1436749 reaction equation
[CH3:1][O:2][CH:3]1[C:8](OC)([O:9]C)[CH2:7][CH2:6][O:5][CH2:4]1.Cl>C1COCC1.O>[CH3:1][O:2][CH:3]1[C:8](=[O:9])[CH2:7][CH2:6][O:5][CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 587845333,4,4-Trimethoxyoxane

Product 1

HCID 235336103-Methoxyoxan-4-one

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 3,4,4-trimethoxytetrahydro-2H-pyran (4 g, 20 mmol) in THF/H2O (60 mL/10mL) was added concentrated HCl (6 mL). After being stirred for 1 h, THF was removed in vacuo. The aqueous solution was extracted with ether (3 ×100 mL). The extracts were dried and concentrated in vacuo to provide the desired product. 1H NMR (CDCl3) δ 4.30-4.10 (2H, m), 3.75-3.65 (2H, m), 3.60-3.50 (1H, m), 3.50 (3H, s), 2.70-2.50 (2H, m).

Workup

  1. customTHF was removed in vacuo
  2. extractionThe aqueous solution was extracted with ether (3 ×100 mL)
  3. customThe extracts were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47a22b06f60f48a49f9f47921e0d48fb
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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