Water → 1,4-Benzenediacetic acid, dimethyl ester

HRID 1790380ノート

反応式

HRID 1790380 の反応式
Br[CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.C[Mg]Br.[OH2:15].[C:16]([O:19][CH2:20]C)(=[O:18])C.[O:22]1[CH2:26]CCC1>C(OCC)C>[C:7]1([CH2:8][C:16]([O:19][CH3:20])=[O:18])[CH:10]=[CH:11][C:4]([CH2:3][C:2]([O:22][CH3:26])=[O:15])=[CH:5][CH:6]=1

参加物

7

反応物 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 110851354-(2-Bromoethyl)benzaldehydeHCID 178418573HCID 178418573、化合物

生成物 1

HCID 5207741,4-Benzenediacetic acid, dimethyl ester収率 83.8%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

4-(2-Bromoethyl)benzaldehyde (3.245 g) was dissolved in tetrahydrofuran (60 ml). Under ice cooling, a 3 M solution (4.9 ml) of methylmagnesium bromide in diethyl ether was added dropwise thereinto and the resultant mixture was stirred for 1.5 hr. After adding water and ethyl acetate, the layers were separated and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (2.745 g) as a brown oil (yield: 83.8%).

後処理

  1. customthe layers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was then purified by silica gel column chromatography (hexane/ethyl acetate system)

出典と根拠

ORDレコード
ord-37b599736875400c8225ce2333f92727
出典データセット
uspto-grants-2006_07
特許番号
US07071201B2

反応ノート

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