Furfural → 2-(1-Hydroxy-2-methyl-3-butynyl)-furan

HRID 2413204Notes

Reaction equation

HRID 2413204 reaction equation
[Al].Br[CH:3]([CH3:6])[C:4]#[CH:5].[CH:7](=[O:13])[C:8]1[O:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[NH4+]>O1CCCC1>[O:12]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:7]([OH:13])[CH:4]([CH3:5])[C:3]#[CH:6]

Participants

6

Reactant 4

HCID 7362FurfuralHCID 25517Ammonium ChlorideHCID 5359268AluminumHCID 109424653-Bromo-1-butyne

Product 1

HCID 133628502-(1-Hydroxy-2-methyl-3-butynyl)-furanYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

Aluminum (5.0 g, 0.18 mole), mercuric chloride (100 mg) and tetrahydrofuran (THF) (70 ml) were added to a reactor, and a solution of 3-bromo-1-butyne (20 g, 0.15 mole) in THF (20 ml) was added dropwise at 40° to 50° C. to prepare a Grignard reagent. Thereafter, to this THF solution of the Grignard reagent was added dropwise a solution of furfural (11.5 g, 0.12 mole) in THF (20 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 100 ml) and extracted with ether. The extract was washed with water, dried and concentrated. The residue obtained was distilled under reduced pressure to obtain 10.4 g (yield, 58%) of pure 1-(2-furyl)-2-methyl-3-butyn-1-ol having a boiling point of 75°-85° C./3 mmHg.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ether
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue obtained
  7. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-b19be6b3b0944811b2c6cb4c85e6b0c3
Source dataset
uspto-grants-1985_01
Patent number
US04496586

Reaction notes

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