Ethyl orthoformate → 3-Bromo-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-methoxy-phenol

HRID 561927

Reaktionsgleichung

[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1.[OH:13][CH2:14][C:15]([CH3:19])([CH2:17]O)[CH3:16].C(OCC)(OCC)OCC>CC1C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[C:7]([CH:8]2[O:13][CH2:14][C:15]([CH3:19])([CH3:17])[CH2:16][O:9]2)=[C:6]([OH:10])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of 6-bromo-2-hydroxy-3-methoxy-benzaldehyde (2.31 g, 10.0 mmol), neopentyl glycol (1.14 g, 11.0 mmol), TsOH (9.5 mg) and triethyl orthoformate (1.93 g, 13.0 mmol) were heated at 110° C. for 30 min and then partitioned between NaHCO3 (300 mL) solution and EtOAc (200 mL). The aqueous layer was extracted with EtOAc (3×30 mL) and the combined extracts were washed with brine and dried through Na2SO4. Evaporation of solvent afforded the title compound (3.17 g, 100%). 1H NMR (CDCl3) δ 0.85 (s, 3H), 1.27 (s, 3H), 3.70 (s, 2H), 3.82 (s, 2H), 3.85 (s, 3H), 5.90 (s, 1H), 6.72 (d, J=8 Hz, 1H), 7.02 (d, J=8 Hz, 1H).

Aufarbeitung

custompartitioned between NaHCO3 (300 mL) solution and EtOAc (200 mL)
extractionThe aqueous layer was extracted with EtOAc (3×30 mL)
washthe combined extracts were washed with brine
dry with materialdried through Na2SO4
customEvaporation of solvent

Quellen und Nachweise

ORD-Eintrag: ord-8ce3b895fef84432bf23310f1f69fcac
Quelldatensatz: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08063225B2

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