Potassium Carbonate → Methyl 2-(5-ethyl-2-formylphenoxy)propanoate

HRID 343282

反応式

HRID 343282 の反応式
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:10]=[O:11])=[C:7]([OH:9])[CH:8]=1)[CH3:2].Br[CH:13]([CH3:17])[C:14]([O-:16])=[O:15].[C:18](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:10]=[O:11])=[C:7]([CH:8]=1)[O:9][CH:13]([CH3:17])[C:14]([O:16][CH3:18])=[O:15])[CH3:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 102360174-Ethyl-2-hydroxybenzaldehydeHCID 14535398Alpha-bromopropionate

生成物 1

HCID 54200069Methyl 2-(5-ethyl-2-formylphenoxy)propanoate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A stirred solution of 21.8 grams (0.15 mole) of 5-ethyl-2-formylphenol, 24.2 grams (0.15 mole) of methyl DL-2-bromopropanoate, and 30 grams (0.22 mole) of potassium carbonate in 300 mL of acetone was heated at reflux for about 18 hours. After this time, the reaction mixture was cooled and concentrated under reduced pressure to a residue. The residue was taken up in methylene chloride, washed first with water, and then with an aqueous 10% sodium hydroxide solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel, using a gradient elution starting with 50% methylene chloride in hexane and progressing to 100% methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 9.8 grams of methyl 2-(5-ethyl-2-formylphenoxy)propanoate. The NMR spectrum was consistent with the proposed structure.

後処理

  1. temperatureat reflux for about 18 hours
  2. temperatureAfter this time, the reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure to a residue
  4. washwashed first with water
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. washa gradient elution
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-cd661f3b94d34d31bf589a901e56bcd2
出典データセット
uspto-grants-1999_01
特許番号
US05861359

関連ノート

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