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

HRID 280712

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][CH2:14][CH2:15][CH3:16])=[CH2:11]>>[CH3:9][CH:4]1[C:5](=[O:8])[C:6]([O:7][CH:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:11])=[C:2]([CH3:1])[O:3]1

Participants

Reactant 2

HCID 8108Butyl vinyl ether

HCID 19309Furaneol

Product 1

HCID 233212752,5-dimethyl-4-[(1'-butoxy)ethoxy]-3(2H)-furanoneYield 38.7%

Procedure

2,5-Dimethyl-4-hydroxy-3(2H)-furanone (13.3 g, 0.1 mole) and butyl vinyl ether (20.0 g, 0.2 mole) are reacted as in Example 1 to give a 37.8% yield (8.83 g) of 2,5-dimethyl-4-[(1'-butoxy)ethoxy]-3(2H)-furanone, b.p. 68.8° C. (0.75 torr) IR (neat, film) 1200, 1625, 1700, 2865, 2930, 2958, 2978 cm-1, 1H NMR (CDCl3) δ0.95 (m, 3), 1.35 (d, J=5 Hz, 3), 1.38 (d, J=8 Hz, 3), 2.18 (S, 3), 3.70 (m, 2), 4.48 (q, J=7 Hz, 1) 5.31 (q, J=5 Hz, 1).

Sources & evidence

ORD record: ord-027e4691c0b5462a968de72458084b16
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04590284

Linked notes

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