Lithium hydroxide, monohydrate → 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoic acid

HRID 20578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20578
O.[OH-].[Li+].[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]([CH3:27])[CH2:24][O:25][CH3:26])[CH:21]=1)[C:15]([O:17]C)=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O.C1COCC1>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@H:23]([CH3:27])[CH2:24][O:25][CH3:26])[CH:21]=1)[C:15]([OH:17])=[O:16])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 59127090methyl 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoate

Produkt 1

HCID 593469053-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoic acidAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (1.30 g, 0.03 mol) in water (40 mL) was added to a solution of methyl 3-(benzyloxy)-5-[(1R)-2-methoxy-1-methylethoxy]benzoate (4.11 g, 0.012 mol) in THF (80 mL) and the reaction mixture stirred for 20 hours at ambient temperature. The THF was removed in vacuo. The aqueous residue was adjusted to pH3 with 1M hydrochloric acid and extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine (50 mL), dried (MgSO4), filtered, and evaporated to give the desired compound (3.79 g).

Aufarbeitung

  1. customThe THF was removed in vacuo
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined extracts were washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ebb519a626cc41c4ab4cb6494984bf4f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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