Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → Methyl 5-chloro-2-(2-chloroethoxy)benzoate

HRID 78492

반응식

HRID 78492 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=1)[OH:6].C1(C)C=CC(S(O[CH2:23][CH2:24][Cl:25])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[Cl:11][C:9]1[CH:8]=[CH:7][C:5]([O:6][CH2:23][CH2:24][Cl:25])=[C:4]([CH:10]=1)[C:3]([O:2][CH3:1])=[O:12]

참가 물질

7

반응물 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 11430Potassium CarbonateHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

생성물 1

HCID 66846837Methyl 5-chloro-2-(2-chloroethoxy)benzoate

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

A mixture of methyl-5-chlorosalicylate (19.5 g, 105 mmol), 2-chloroethyl p-toluenesulfonate (19.3 mL, 107 mmol) and K2CO3 (28.9 g, 210 mmol) in 105 mL of N,N-dimethylformamide was warmed to 50° C. and allowed to stir for 18 hours. The mixture was cooled to ambient temperature, diluted with 25 mL of ethyl acetate and 25 mL of H2O. The layers were separated and the organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 75% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 249 (M+H)+, 266 (M+NH4)+.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification via column chromatography (SiO2, 75% hexanes in ethyl acetate)

출처 및 근거

ORD 기록
ord-191942b1cd1f4610a6c345a57cd8f0b7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841334B2

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