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

HRID 257356

반응식

HRID 257356 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-efb1b7ad488b4c87892270c806498fbd
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262390

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