Sodium ethoxide → Furaneol

HRID 1449127노트

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HRID 1449127 반응식
[O-]CC.[Na+].[C:5]([C:10]1[O:11][C:12]([CH3:17])=[C:13]([OH:16])[C:14]=1[OH:15])(OCC)=O>CN(C)C=O.C1(C)C=CC=CC=1>[OH:15][C:14]1[C:13](=[O:16])[CH:12]([CH3:17])[O:11][C:10]=1[CH3:5]

참가 물질

5

반응물 2

HCID 2723922Sodium ethoxideHCID 54719681Ethyl 5-methyl-3,4-dihydroxy-2-furoate

생성물 1

HCID 19309Furaneol수율 65%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

In a 1 L three-necked flask fitted with a mechanical stirrer and a gas inlet tube is placed a suspension of 34 g of sodium ethoxide in a mixture of 100 ml of dimethylformamide and 300 ml of toluene. To the stirred suspension is added at room temperature, under nitrogen, 93 g of 2-carbethoxy-5-methyl-3,4-dihydroxy-furan. Gaseous methyl bromide is bubbled through the stirred reaction mixture at 30°-40° C. till the pH of the reaction mixture reaches 6.5-7.0. The solvents are removed under vacuum and the residue is dissolved in a solution of 80 g of sodium hydroxide in 350 ml of water. The reaction mixture is kept at room temperature under nitrogen for 20 hours, acidified with hydrochloric acid and continuously extracted with ether. The ether extract is dried and the solvent removed under vacuum, the residue is recrystallized from ether, yielding 41.5 g (65%) of 4-hydroxy-2,5-dimethyl-3-oxo-2H-furan, m.p. 81.5°-83.1° C.

후처리

  1. customIn a 1 L three-necked flask fitted with a mechanical stirrer and a gas inlet tube
  2. additionTo the stirred suspension is added at room temperature, under nitrogen
  3. customGaseous methyl bromide is bubbled through the stirred reaction mixture at 30°-40° C. till the pH of the reaction mixture
  4. customThe solvents are removed under vacuum
  5. dissolutionthe residue is dissolved in a solution of 80 g of sodium hydroxide in 350 ml of water
  6. extractioncontinuously extracted with ether
  7. extractionThe ether extract
  8. customis dried
  9. customthe solvent removed under vacuum
  10. customthe residue is recrystallized from ether

출처 및 근거

ORD 기록
ord-be92873ff3324515ba8d63c18b0c931b
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04189439

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