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

HRID 78492

反応式

HRID 78492 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-191942b1cd1f4610a6c345a57cd8f0b7
出典データセット
uspto-grants-2014_09
特許番号
US08841334B2

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