Furfuryl Alcohol → 6-Acetoxy-2H-pyran-3(6H)-one

HRID 2170522Notes

Reaction equation

HRID 2170522 reaction equation
[CH2:1]([OH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].[C:13]([O-:16])(=[O:15])[CH3:14].[Na+].BrN1C(=O)CCC1=O.C(OC(=O)C)(=O)C>O.C1COCC1>[C:13]([O:16][CH:5]1[CH:4]=[CH:3][C:1](=[O:7])[CH2:2][O:6]1)(=[O:15])[CH3:14]

Participants

8

Reactant 5

HCID 7361Furfuryl Alcohol2×HCID 7918Acetic AnhydrideHCID 67184N-bromobutanimideHCID 516892Sodium Bicarbonate2×HCID 517045Sodium Acetate

Product 1

HCID 111162906-Acetoxy-2H-pyran-3(6H)-oneYield 42.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

500 g (5.10 mol) of furfuryl alcohol (Compound 1) was dissolved in 1.65 L of water and 6.6 L of THF in a nitrogen gas stream and cooled to 0° C. or lower. To this, a mixture of 855 g (10.2 mol) of sodium hydrogen carbonate, 418 g (5.10 mol) of sodium acetate and 953 g (5.35 mol) of N-bromosuccinimide was added by spending 40 minutes. Thereafter, the resultant was agitated for an hour, and 2,083 g (20.4 mol) of acetic anhydride was added at 0° C. or lower. Then, the resultant was heated to room temperature and agitated overnight. At the end of the reaction, 20.5 L of a saturated aqueous sodium hydrogen carbonate solution was added, followed by extraction with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and subjected to vacuum concentration to obtain 776 g of a crude product (crude yield: 42.6%). The obtained crude product was subjected to column purification (n-Hex:AcOEt=3:1) to obtain 339 g of Compound (±) 4 as a yellow-brown oily product.

Workup

  1. additionwas added
  2. stirringagitated overnight
  3. additionwas added
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationsubjected to vacuum concentration
  7. customto obtain 776 g of a crude product (crude yield: 42.6%)
  8. customThe obtained crude product
  9. customwas subjected to column purification (n-Hex:AcOEt=3:1)

Sources & evidence

ORD record
ord-d61f8eebc6cc4320a14f4e5006875623
Source dataset
uspto-grants-2015_06
Patent number
US09051288B2

Reaction notes

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