Hydroxyphenylacetic acid → [(4-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)]acetic acid

HRID 899871

Reaktionsgleichung

Reaktionsgleichung von HRID 899871
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[OH-].[K+].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23]Br>C(O)C>[CH3:14][O:15][C:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)=[O:25]

Komponenten

5

Edukt 3

HCID 127Hydroxyphenylacetic acidHCID 14797Potassium HydroxideHCID 2734813Methyl 2-(bromomethyl)benzoate

Produkt 1

HCID 68869545[(4-{[2-(Methoxycarbonyl)benzyl]oxy}phenyl)]acetic acidAusbeute 17,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-Hydroxyphenylacetic acid (760 mg, 4.995 mmol) was dissolved in ethanol (99.5%, 20 ml). Potassium hydroxide (560.5 mg, 9.99 mmol) was added. The mixture was stirred at room temperature for 30 minutes. 2-Bromomethylbenzoic acid methyl ester (1144.2 mg, 4.995 mmol) was then dropped in. The resulting mixture was heated to reflux for 2 hours and then evaporated in vacuum to dry. Water and ethyl acetate were added into the residue and the phases were separated. The water phase was acidified with 10% hydrochloric acid, pH˜5, and then extracted with ethyl acetate. The organic phase was dried with magnesium sulphate and evaporated in vacuum to dry. Chromatography of the residue on a column (ISOLUTE® SI, 5 g/6 ml) using DCM, MeOH/DCM (1:99) as eluant gave the desired product (262 mg), yield 17.5%.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. customevaporated in vacuum
  4. customto dry
  5. additionWater and ethyl acetate were added into the residue
  6. customthe phases were separated
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic phase was dried with magnesium sulphate
  9. customevaporated in vacuum
  10. customto dry

Quellen und Nachweise

ORD-Eintrag
ord-bfa187513f6b4568a95bd65ebf51f325
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07355069B2

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