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Acetaldehyde → 2-(1-hydroxyethyl)-3-hydroxy-6-methyl-pyran-4(1H)-one

HRID 1249781
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HRID 1249781 반응식
[CH3:1][C:2]1[O:8][CH:7]=[C:6]([OH:9])[C:4](=[O:5])[CH:3]=1.[CH:10](=[O:12])[CH3:11]>O>[OH:12][CH:10]([C:7]1[O:8][C:2]([CH3:1])=[CH:3][C:4](=[O:5])[C:6]=1[OH:9])[CH3:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 177AcetaldehydeHCID 695214H-Pyran-4-one, 5-hydroxy-2-methyl-

생성물 1

HCID 107972282-(1-hydroxyethyl)-3-hydroxy-6-methyl-pyran-4(1H)-one수율 83%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

Allomaltol (12.6 g, 100 mmol, 1 eq.) was added to 100 ml water and the pH of the solution was adjusted to 10.5 using 50% aqueous sodium hydroxides. Acetaldehyde (5.5 g, 125 mmol, 1.25 eq.) dissolved in 25 ml water was slowly added dropwise over 1 hour and the solution allowed to stir overnight. After adjustment to pH 1 with 37% hydrochloric acid, the reaction mixture was extracted with 3×150 ml of dichloromethane. The combined organic extracts were dried over anhydrous sodium sulphate, filtered and concentrated to yield the crude product. Recrystallisation from toluene afforded the pure product (14.1 g, 83%) as white needles. m.p. 127-130° C. [lit. 126-128° C.]. Ellis (1993)

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후처리

  1. additionwas slowly added dropwise over 1 hour
  2. extractionAfter adjustment to pH 1 with 37% hydrochloric acid, the reaction mixture was extracted with 3×150 ml of dichloromethane
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield the crude product
  7. customRecrystallisation from toluene

출처 및 근거

ORD 기록
ord-7122cd02109f4645bcf99a051f9e8f7e
출처 데이터셋
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06335353B1

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