Homophthalic acid → 3-(4-Methoxybenzyl)isocoumarin

HRID 432667

Reaktionsgleichung

[C:1]([OH:13])(=O)[CH2:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5]([OH:7])=O.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]C(Cl)=O)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:1]2[O:13][C:5]([C:4]3[C:3]([CH:2]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:7])=[CH:18][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 200 °C

Versuchsvorschrift

A well-stirred mixture of homophthalic acid (10 g; 56 mmol) and 2-(4-methoxyphenyl)acetyl chloride (10 g, 230 mmol) was heated at 200° C. for 3 hours under nitrogen then cooled to 50° C. and dissolved in toluene (100 ml), The solvent was removed in vacuo and the residue was dissolved in methanol (100 ml). Silica (30 g) was added and the solvent was removed in vacuo. The crude product, thereby adsorbed onto silica, was applied to the top of a column of silica and purified by chromatography using 10-50% mixtures of ethyl acetate and hexane as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 3-(4-methoxybenzyl)isocoumarin (0.9 g, 26%) as an oil; δH 3.75 (3H, s), 3.80 (2H, s), 6.50 (1H, s), 6.95 (2H, d, J=8.9 Hz), 7.30 (2H, d, J=8.9 Hz), 7.40-7.90 (3H, m), 8.10 (1H, d); m/z (M+H)+. 267.

Aufarbeitung

temperaturethen cooled to 50° C.
customThe solvent was removed in vacuo
dissolutionthe residue was dissolved in methanol (100 ml)
additionSilica (30 g) was added
customthe solvent was removed in vacuo
custompurified by chromatography
customthe solvents removed in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-63120e174dd04a94ac4274466862b099
Quelldatensatz: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06664269B2

Verknüpfte Notizen

Wird geladen…