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

HRID 1380810ノート

反応式

HRID 1380810 の反応式
[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]

参加物

6

反応物 4

HCID 527PropanalHCID 971Oxalic AcidHCID 7288Ethyl ketone2 回HCID 14797Potassium Hydroxide2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
15 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7c7aaa02eadc48fbb29257466918f115
出典データセット
uspto-grants-1986_04
特許番号
US04584193

反応ノート

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