Hydroxide → HCID 53806682, compound

HRID 359378Notes

Reaction equation

HRID 359378 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[CH3:8][C:9]1([CH3:16])[C:13](=[O:14])[CH:12]=[C:11]([CH3:15])[O:10]1.[OH-].[Cl-].[Na+]>C(O)C>[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=[CH:15][C:11]2[O:10][C:9]([CH3:16])([CH3:8])[C:13](=[O:14])[CH:12]=2)=[CH:2]1

Participants

6

Reactant 4

HCID 961HydroxideHCID 5234Sodium ChlorideHCID 103513-FuraldehydeHCID 1370803(2H)-Furanone, 2,2,5-trimethyl-

Product 1

HCID 53806682HCID 53806682, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-furaldehyde (1.26 g, 13.2 mM) and 2,2,5-trimethyl-3(2H)-furanone (1.5 g, 11.9 mM) in ethanol (50mL), was added 1N aqueous hydroxide (1.2 mL, 1.2 mM). After the reaction solution was stirred for one day at room temperature, saturated aqueous sodium chloride (400 mL) was added. The aqueous layer was extracted with diethyl ether (3×100 mL). The combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated to give a yellow solid. The crude product was purified by chromatography (silica gel, hexane-ethyl acetate) to yield yellow crystals (1.8 g, 74% yield), m.p. 79°-80° C.

Workup

  1. extractionThe aqueous layer was extracted with diethyl ether (3×100 mL)
  2. washThe combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow solid
  7. customThe crude product was purified by chromatography (silica gel, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7c4ecd7564154ce6b6ffe83225852aa8
Source dataset
uspto-grants-1991_03
Patent number
US05001126

Reaction notes

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