Furfural → HCID 11788394, compound

HRID 2413202Notes

Reaction equation

HRID 2413202 reaction equation
[Mg].[CH2:2](Cl)[CH:3]=[CH:4][CH3:5].ClC(C)C=C.[CH:12](=[O:18])[C:13]1[O:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>O1CCCC1>[O:17]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH:12]([OH:18])[CH:4]([CH3:5])[CH:3]=[CH2:2]

Participants

7

Reactant 5

HCID 7362FurfuralHCID 112423-Chloro-1-buteneHCID 11589Crotyl chlorideHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 11788394HCID 11788394, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

Magnesium (36 g, 1.5 mole) and tetrahydrofuran (THF) (300 ml) were added to a reactor, and a solution of crotyl chloride or 3-chloro-1-butene (118 g, 1.8 mole) in THF (100 ml) was added dropwise at 30° to 35° C. to prepare a Grignard reagent. Thereafter, to this THF solution of the Grignard reagent was added dropwise a solution of furfural (106 g, 1.1 mole) in THF (150 ml) at 20° to 30° C. over about 1 hour, followed by stirring at room temperature for further 2 hours. After completion of the reaction, the reaction solution was poured into an aqueous ammonium chloride solution (about 500 ml), followed by extraction with ether. The ether extract was washed with water, dried and concentrated, and the residue obtained was distilled under reduced pressure to obtain 150 g (yield, 90%) of pure 1-(2-furyl)-2-methyl-3-buten-1-ol having a boiling point of 95°-107° C./25 mmHg.

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated
  7. customthe residue obtained
  8. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-50d0eea3e396417f83f0293318d469d2
Source dataset
uspto-grants-1985_01
Patent number
US04496586

Reaction notes

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