Ethyl vinyl ether → 2,5-dimethyl-4-[(1'-ethoxy)ethoxy]-3(2H)-furanone

HRID 280711Notes

Reaction equation

HRID 280711 reaction equation
[CH3:1][CH:2]1[C:6](=[O:7])[C:5]([OH:8])=[C:4]([CH3:9])[O:3]1.[CH:10]([O:12][CH2:13][CH3:14])=[CH2:11].C(=O)(O)[O-].[Na+]>Cl>[CH3:9][CH:4]1[C:5](=[O:8])[C:6]([O:7][CH:10]([O:12][CH2:13][CH3:14])[CH3:11])=[C:2]([CH3:1])[O:3]1

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 19309FuraneolHCID 516892Sodium Bicarbonate

Product 1

HCID 233212762,5-dimethyl-4-[(1'-ethoxy)ethoxy]-3(2H)-furanoneYield 80.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

To a heterogenous solution of 2,5-dimethyl-4-hydroxy-3-(2H)-furanone (133.0 g, 1.0 mole) and ethyl vinyl ether (144.0 g, 2.0 moles) at 10° C., under N2, is added dropwise, concentrated hydrochloric acid (1.0 g). The temperature rises to 11° C. and the solution becomes homogeneous. It is stirred for 1.5 hours, and then the coolant is removed. Stirring is continued at room temperature for an additional six hours, after which the reaction is quenched by the addition of solid sodium bicarbonate (10 g, 0.12 mole). The reaction mixture is washed with 100 ml water and a second time with 100 ml of 5% NaHCO3. The product is dried over Na2SO4 and distilled to give a 78.9% yield (161.8 g) of 2,5-dimethyl-4-[(1'-ethoxy)ethoxy]-3(2H)-furanone, b.p. 91° C. (0.05 torr), IR (neat, film) 1200, 1625, 1700, 2030, 2978 cm-1 ; 1H NMR (CDCl3) δ1.20 (t, J=8 Hz, 3), 1.32 (d, J=5 Hz, 3), 1.42 (d, J=7 Hz, 3), 2.2 (S, 3), 3.72 (m, 2), 4.48 (q, J=7 Hz, 1), 5.32 (q, J=5 Hz, 1).

Workup

  1. customrises to 11° C.
  2. customthe coolant is removed
  3. stirringStirring
  4. waitis continued at room temperature for an additional six hours
  5. washThe reaction mixture is washed with 100 ml water
  6. dry with materialThe product is dried over Na2SO4
  7. distillationdistilled

Sources & evidence

ORD record
ord-4dcb7ad850974758914ce18c7de99969
Source dataset
uspto-grants-1986_05
Patent number
US04590284

Reaction notes

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