Hydrochloric Acid → Methyl 4-[(2-benzyloxyphenyl)hydroxymethyl]benzoate

HRID 1982807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1982807
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[CH3:17][O:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][CH:22]=1)=[O:20].Cl>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:27]([OH:28])[C:24]1[CH:23]=[CH:22][C:21]([C:19]([O:18][CH3:17])=[O:20])=[CH:26][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 15294Methyl 4-FormylbenzoateHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 5462224Magnesium

Produkt 1

HCID 21909317Methyl 4-[(2-benzyloxyphenyl)hydroxymethyl]benzoateAusbeute 37,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A Grignard reagent was prepared from 2-benzyloxybromobenzene (5.3 g), magnesium (0.49 g) and tetrahydrofuran (160 mL). The obtained Grignard reagent was added to a solution of methyl terephthalaldehydate (3.3 g) in tetrahydrofuran (60 mL), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added water and dilute hydrochloric acid, and the mixture was extracted with ethylacetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=4/1) to give methyl 4-[(2-benzyloxyphenyl)-hydroxymethyl]benzoate (2.6 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethylacetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on aminopropyl silica gel (eluent: hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-894a099644a84e08943560c4073f4008
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07541341B2

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