Furan, 2,2'-[oxybis(methylene)]bis- → 2-{[(Furan-2-yl)methoxy]methyl}-5-methylfuran

HRID 1579657Notes

Reaction equation

HRID 1579657 reaction equation
[CH2:1]([O:7][CH2:8][C:9]1[O:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH3:14]C1OC(CBr)=CC=1>CCOCC>[CH2:8]([O:7][CH2:1][C:2]1[O:6][C:5]([CH3:14])=[CH:4][CH:3]=1)[C:9]1[O:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 263034Furan, 2,2'-[oxybis(methylene)]bis-HCID 122459262-(Bromomethyl)-5-methylfuran

Product 1

HCID 205603562-{[(Furan-2-yl)methoxy]methyl}-5-methylfuran

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1 d. 5-Methyl-furfuryl furfuryl ether was prepared by the procedure described by J. E. Zanetti in J. Am. Chem. Soc. 49, 1066 (1927) for the difurfuryl ether, starting with 5-methylfurfuryl bromide (Compt.Rend. 222, 1441 (1946)) instead of furfuryl bromide of Zanetti. The product was isolated by ether extraction of the crude mixture after having diluted with water. For purification the ether extract was distilled twice - b.p. 68°-70°C. at 0.01 mm./Hg vacuum. The product was a viscous colourless liquid, darkening rapidly on contact with air.

Workup

  1. custom1 d

Sources & evidence

ORD record
ord-37b52a200b874f52ae6f33cdf97532e6
Source dataset
uspto-grants-1976_01
Patent number
US03931246

Reaction notes

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