Water → HCID 11019639, compound

HRID 1838787Notes

Reaction equation

HRID 1838787 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH:14]=O.[Cl-].[Li+].O>CN1CCN(C)C1=O>[CH2:14]([C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:1]=1[OH:8])[OH:7])[C:10]1[O:9][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7362FurfuralHCID 125111,4-CyclohexanedioneHCID 433294Lithium Chloride

Product 1

HCID 11019639HCID 11019639, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of 1,4-cyclohexanedione (5.6 g; 50 mmol), furan-2-carbaldehyde (4.8 g; 50 mmol) and anhydrous lithium chloride (2.1 g; 50 mmol) in 1,3-dimethyl-2-imidazolidinone (20 ml) was heated with stirring over an a oil bath at atmospheric pressure. The temperature of the bath was maintained at 165° C. for 1 h. The cooled reaction mixture was poured into water (300 ml) and extracted with ethyl acetate (2×150 ml). The combined organic layers were washed with water (2×100 ml), dried over magnesium sulphate and filtered. The organic solvent was removed in vacuo. The residue (9.4 g) was purified by flash chromatography using a silica gel column and toluene/ethyl acetate (90:10) as eluent, to give 6.7 g (70%) of 3-furfurylhydroquinone.

Workup

  1. temperaturewas heated
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate (2×150 ml)
  4. washThe combined organic layers were washed with water (2×100 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customThe organic solvent was removed in vacuo
  8. customThe residue (9.4 g) was purified by flash chromatography

Sources & evidence

ORD record
ord-e660d1e57d044a42aa799c5eba788397
Source dataset
uspto-grants-2004_01
Patent number
US06676851B1

Reaction notes

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