Hydrochloric Acid → 2,5-Furandimethanol

HRID 1921602Notes

Reaction equation

HRID 1921602 reaction equation
B.[Na].C([O:5][CH2:6][C:7]1[O:8][C:9]([CH:12]=[O:13])=[CH:10][CH:11]=1)=O.Cl.C(=O)([O-])O.[Na+]>C(O)C>[OH:5][CH2:6][C:7]1[O:8][C:9]([CH2:12][OH:13])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58489132HCID 58489132, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 746632,5-Furandimethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borane (1.2 g, 32 mmol) was added to a solution of 5-formylfuran-2-yl-methyl formate (5.05 g, 30 mmol) in absolute ethanol (150 mL) at 0° C. Then it was warmed to room temperature and stirred for 48 hours. Then it was cooled to 0° C. and acidified with concentrated hydrochloric acid to pH 4 and then neutralized immediately with 5% sodium hydrogen carbonate solution. The mixture was filtered and the filtrate was evaporated to dryness under vacuum. The residue was taken up in ethanol (30 mL), filtered, and the filtrate was concentrated to dryness.

Workup

  1. temperatureThen it was cooled to 0° C.
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness under vacuum
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-54cbb5860d514f7197452c439eac4031
Source dataset
uspto-grants-2012_05
Patent number
US08173700B2

Reaction notes

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