Acetylresorcinol → Acetic acid 3-cyclobutoxy-phenyl ester

HRID 497531

Reaktionsgleichung

Reaktionsgleichung von HRID 497531
[OH:1][C:2]1[CH:3]=[C:4]([O:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH:12]1(O)[CH2:15][CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH:12]1([O:1][C:2]2[CH:3]=[C:4]([O:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=2)[CH2:15][CH2:14][CH2:13]1

Komponenten

6

Edukt 4

HCID 5055AcetylresorcinolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 76218Cyclobutanol

Produkt 1

HCID 20872617Acetic acid 3-cyclobutoxy-phenyl esterAusbeute 20,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Acetic acid 3-hydroxy-phenyl ester (1 ml, 9 mmol) was mixed with cyclobutanol (0.58 g, 8 mmol), triphenylphosphine (2.1 g, 8 mmol) and diisopropyl azodicarboxylate (1.57 ml, 8 mmol) in tetrahydrofuran (20 ml) at 0° C. under a nitrogen atmosphere. The mixture was warmed to room temperature and stirred for 16 hours. The reaction mixture was concentrated in-vacuo the residue was purified by chromatography on silica gel using ethyl acetate in pentane as eluant (gradient from 0:100 to 15:85) to give acetic acid 3-cyclobutoxy-phenyl ester (340 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in-vacuo the residue
  2. customwas purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-62f950fde7ec43f39671d9e5e2499b64
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949573B2

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