Potassium Carbonate → Methyl 2-(5-chloro-2-formylphenoxy)propionate

HRID 257356

反応式

HRID 257356 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5](=[CH:8][CH:9]=1)[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH:3]=1)[O:10][CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 5201014-Chloro-2-hydroxybenzaldehyde

生成物 1

HCID 53800060Methyl 2-(5-chloro-2-formylphenoxy)propionate収率 18.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 22.0 g (0.141 mole) of 4-chlorosalicylaldehyde, 30 g (0.22 mole) of anhydrous potassium carbonate, and 30.0 g (0.184 mole) of methyl 2-bromopropionate in 120 mL of N,N-dimethylformamide was heated at 80° C. for approximately 17 hours. At the end of that period, the reaction mixture was poured over ice and extracted successively with diethyl ether and ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate, and filtered. The solvents were then evaporated under reduced pressure, leaving a residue weighing 20 g. This residue was purified by placing it on a silica gel column and eluting with diethyl ether/petroleum ether (25/75). After the product-containing fractions were combined and the solvents evaporated under reduced pressure, 6.23 g of methyl 2-(5-chloro-2-formylphenoxy)propionate was isolated as a yellow liquid. Similarly, other fractions were combined and evaporated, yielding 1.69 g of methyl 2-(3-chloro-2-formylphenoxy)propionate as a yellow liquid. The NMR spectra of both compounds were consistent with proposed structure of each. This reaction was repeated several times.

後処理

  1. additionAt the end of that period, the reaction mixture was poured over ice
  2. extractionextracted successively with diethyl ether and ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvents were then evaporated under reduced pressure
  7. customleaving a residue
  8. customThis residue was purified
  9. washeluting with diethyl ether/petroleum ether (25/75)
  10. customthe solvents evaporated under reduced pressure

出典と根拠

ORDレコード
ord-efb1b7ad488b4c87892270c806498fbd
出典データセット
uspto-grants-1993_11
特許番号
US05262390

関連ノート

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