Furfural → 1-(Furan-2-yl)but-3-en-1-ol

HRID 1085312Notes

Reaction equation

HRID 1085312 reaction equation
[CH:1](=[O:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[Br-].[NH4+].O1C[CH2:13][CH2:12][CH2:11]1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[OH:7][CH:1]([C:2]1[O:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][CH:12]=[CH2:11]

Participants

6

Reactant 4

HCID 7362FurfuralHCID 8028TetrahydrofuranHCID 25514Ammonium BromideHCID 25517Ammonium Chloride

Product 1

HCID 2530521-(Furan-2-yl)but-3-en-1-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Reaction and after-treatment were carried out in the same manner as in Example 3 except that an equimolar amount of furfural was used in place of 5-methylfurfural, and that ammonium bromide and tetrahydrofuran were used in place of ammonium chloride and toluene, respectively, in the same weights as those of the latter, to obtain 50.6 g of the fraction of 2-(1-hydroxy-3-butenyl)-furan (content, 99.3%) (yield, 91.0%).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-f18e2fa4f5364ee6bc6a5b4e1034cc19
Source dataset
uspto-grants-1991_04
Patent number
US05008410

Reaction notes

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