Diethyl 2-benzylpropanedioate → 2-Benzylpropane-1,3-diol

HRID 839726

Reaktionsgleichung

Reaktionsgleichung von HRID 839726
[CH2:1]([CH:8]([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)C>[CH2:1]([CH:8]([CH2:9][OH:10])[CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 69090Diethyl 2-benzylpropanedioate

Produkt 1

HCID 5202412-Benzylpropane-1,3-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Diethyl benzylmalonate (100g.) was added dropwise to a stirred suspension of lithium aluminimum hydride (12g.) in anhydrous diethyl ether (300ml.) at 0° C. under argon. The reaction mixture was then stirred overnight at room temperature and worked up by the conventional procedure, described in J. Org. Chem. 1953, 18, 1190. Evaporation of the ether solution gave 2-benzylpropane-1,3-diol. Phosphorus tribromide (26ml.) was added dropwise to this diol (44g.), whilst stirring at 75° C. After the vigorous reaction had ceased, the temperature was raised to 100° C. and maintained at this temperature overnight. The cooled mixture was poured into ice water (500ml.) and extracted with diethyl ether (2 × 500ml.). The combined ether extracts were washed with aqueous sodium bicarbonate, then brine, dried over sodium sulphate and the ether was evaporated. Distillation of the crude product in vacuo gave 2-benzyl-1,3-dibromopropane b.p. 116°-121° C./1.0 mm. Hg.

Aufarbeitung

  1. customEvaporation of the ether solution

Quellen und Nachweise

ORD-Eintrag
ord-0cd061d8a2c44d2797dd96e7e950683c
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04096337

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