Hydrochloric Acid → 4-Allyl-3,5-dihydroxy-benzoic acid methyl ester

HRID 1643554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643554
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([O:10]COC)[C:7]([CH2:14][CH:15]=[CH2:16])=[C:6]([O:17]COC)[CH:5]=1.Cl>CO>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:5]=[C:6]([OH:17])[C:7]([CH2:14][CH:15]=[CH2:16])=[C:8]([OH:10])[CH:9]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 59560396Methyl 4-allyl-3,5-bis(methoxymethoxy)benzoate

Produkt 1

HCID 537917924-Allyl-3,5-dihydroxy-benzoic acid methyl esterAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4-allyl-3,5-bis-methoxymethoxy-benzoic acid methyl ester (10a) (513 mg, 1.73 mmol) in MeOH (4 mL) was added 4N HCl (4 mL). The reaction mixture was stirred at room temperature overnight. The mixture was quenched with H2O (80 mL) and extracted with EtOAc (2×80 mL). The organic layers were dried over MgSO4 and concentrated to give yellow oil which was purified by flash column chromatography eluting with 15-25% EtOAc in hexanes to give a pale yellow solid (285 mg, 79% yield). 1H NMR (400 MHz, CDCl3) δ 7.20 (s, 2 H) 5.95-6.06 (m, J=5.31, 5.31 Hz, 1 H) 5.76-5.82 (m, 2 H) 5.15-5.20 (m, 1 H) 5.12-5.15 (m, 1 H) 3.90 (s, 3 H) 3.50-3.55 (m, 2 H); LCMS for C11H12O4S m/z 209.10 (M+H+).

Aufarbeitung

  1. customThe mixture was quenched with H2O (80 mL)
  2. extractionextracted with EtOAc (2×80 mL)
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customto give yellow oil which
  6. customwas purified by flash column chromatography
  7. washeluting with 15-25% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ffaffcbe2ce04c17a16470630eab789b
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119624B2

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