Acetic Acid → 1-Benzyl-2-chloromethylnaphthalene

HRID 1275420

Reaktionsgleichung

[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]C=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:20](O)(=O)[CH3:21].[ClH:24].P(=O)(O)(O)O>O>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:20]=1[CH2:21][Cl:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

1-Benzylnaphthalene (3.0 g; 13.7 mMol), as prepared above, formaldehyde (1.0 g; 35.7 mMol), glacial acetic acid (4.3 g; 71.7 mMol), concentrated hydrochloric acid (6.5 mL) and 85% phosphoric acid (4.3 mL) were combined and heated in an oil bath maintained at 90° C. for 4.5 hr. The reaction mixture was cooled, a small amount of water was added, and extraction was carried out with diethyl ether. The combined organic extractions were washed with sodium carbonate (10% aqueous), and brine; then dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue subjected to medium pressure chromatography on silica gel eluting with hexane. The product (1.18 g; 32% yield) was isolated as a colorless oil which subsequently crystallized.

Aufarbeitung

temperatureheated in an oil bath
temperatureThe reaction mixture was cooled
extractionextraction
extractionThe combined organic extractions
washwere washed with sodium carbonate (10% aqueous), and brine
dry with materialthen dried over magnesium sulfate
customThe solvent was removed under reduced pressure
customThe product (1.18 g; 32% yield) was isolated as a colorless oil which
customsubsequently crystallized

Quellen und Nachweise

ORD-Eintrag: ord-703b44c124f74a87a1d4ca06178ead62
Quelldatensatz: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06160175

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