Water → Methyl 6-(Hydroxymethyl)-2-naphthoate

HRID 463034

Reaktionsgleichung

Reaktionsgleichung von HRID 463034
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH:10]=[CH:9]2)(=O)C.C([O-])([O-])=O.[K+].[K+].O>CO>[OH:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH:10]=[CH:9]2

Komponenten

5

Edukt 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 15589961Methyl 6-Acetoxymethyl-2-naphthoate

Produkt 1

HCID 11127663Methyl 6-(Hydroxymethyl)-2-naphthoateAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 0.9 g (3.49 mmol) of methyl 6-acetoxymethyl-2-naphthoate in 100 mL of MeOH was added 0.5 g (3.62 mmol) of K2CO3 and 1 mL of H2O. The mixture was stirred at room temperature for 30 min before being evaporated to dryness. The residue was taken up in 50 mL of EtOAc and 30 mL of H2O. The organic layer was dried (Na2SO4) and evaporated to give 0.76 g (100% yield) of methyl 6-hydroxymethyl-2-naphthoate as white crystals: mp 123°-124° C.; IR (mull) 3250, 1720, 1300, 1200, 1130, 1100, 1040, 1020, 920, 900, 840, 820, 760 cm-1 ; 1H NMR (CDCl3) δ2.13 (s, 1, OH), 3.98 (s, 3, CO2CH3), 4.88 (s, 2, CH2OH), 7.3-8.7 (m, 6, ArH); MS calcd for C13H12O3 216.0786, found 216.0787.

Aufarbeitung

  1. custombefore being evaporated to dryness
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-09c9d1179af345c1999fa29104c63438
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04518609

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