Hydrochloric Acid → Methyl 5-(hydroxymethyl)-2-methoxybenzoate

HRID 323406

Reaktionsgleichung

Reaktionsgleichung von HRID 323406
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].O1CCCC1.O1CCCC1.B.Cl>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2723981Borane;tetrahydrofuran2×HCID 10856352Methyl 5-formyl-2-methoxybenzoate

Produkt 1

HCID 18465013Methyl 5-(hydroxymethyl)-2-methoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Combine methyl 2-methoxy-5-formylbenzoate (0.1 g, 0.5 mmol) and tetrahydrofuran (2 mL). Cool in an ice bath. Add a solution of borane tetrahydrofuran complex (0.17 mL, 1 M in tetrahydrofuran, 0.17 mmol). After 1.5 hours, again add a solution of borane tetrahydrofuran complex (0.17 mL, 1 M in tetrahydrofuran, 0.17 mmol). After 2 hours, add a 1 M aqueous solution of hydrochloric acid (2 mL) and stir. After 15 minutes, dilute the reaction mixture with ethyl acetate. Separate the layers, extract the aqueous layer three times with ethyl acetate and combine the organic layers. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give methyl 2-methoxy-5-hydroxymethylbenzoate: Rf=0.32 (silica gel, ethyl acetate).

Aufarbeitung

  1. temperatureCool in an ice bath
  2. waitAfter 2 hours
  3. waitAfter 15 minutes
  4. customSeparate the layers
  5. extractionextract the aqueous layer three times with ethyl acetate
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-42a1c33b2e044642aa67700e7383a44c
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211199B1

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