Propanal → 5-Hydroxy-4-methylheptan-3-one

HRID 1380810노트

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HRID 1380810 반응식
[CH3:1][CH2:2][C:3](=[O:6])[CH2:4][CH3:5].[OH-].[K+].[CH:9](=O)CC.[C:13]([OH:18])(=O)[C:14](O)=O>CO>[CH3:1][CH2:2][C@@H:3]([OH:6])[C@@H:4]([C:13]([CH2:14][CH3:9])=[O:18])[CH3:5]

참가 물질

6

반응물 4

HCID 527PropanalHCID 971Oxalic AcidHCID 7288Ethyl ketone2회HCID 14797Potassium Hydroxide2회

생성물 1

HCID 1556635-Hydroxy-4-methylheptan-3-one

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
15 °C

실험 절차

A 1-liter, 2-necked flask equipped with a dropping funnel, thermometer, and magnetic stirrer was charged with 344.0 g. (4 moles) of freshly distilled 3-pentanone. After cooling the apparatus to 15° C., an addition was made of 30.6 ml. of 16.8% (w/w) potassium hydroxide in methanol. This was followed by dropwise addition over 4 hrs. of 58.0 g. (1 mole) of freshly distilled propionaldehyde mixed with another 172.0-g. lot of 3-pentanone. Stirring was continued for an additional 30 min. after which the base (KOH) was neutralized with 3.5 g. of anhydrous oxalic acid. The solution was filtered and then distilled under vacuum to remove unreacted 3-pentanone and methanol. The aldol distilled at 70° C. (0.45 mm.) and yielded 66.7 g. (46% based on propionaldehyde). The distribution of R*S* and R*R* diastereomers was approximately 1:1.

후처리

  1. customA 1-liter, 2-necked flask equipped with a dropping funnel
  2. additionthermometer, and magnetic stirrer was charged with 344.0 g
  3. additionan addition
  4. additionThis was followed by dropwise addition over 4 hrs
  5. filtrationThe solution was filtered
  6. distillationdistilled under vacuum
  7. customto remove unreacted 3-pentanone and methanol
  8. distillationThe aldol distilled at 70° C. (0.45 mm.)
  9. customyielded 66.7 g

출처 및 근거

ORD 기록
ord-7c7aaa02eadc48fbb29257466918f115
출처 데이터셋
uspto-grants-1986_04
특허 번호
US04584193

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