p-Toluenesulfonic acid → trans 4-(Bromomethyl)-2-methoxy-1,3-dioxolane

HRID 365763

Reaktionsgleichung

Reaktionsgleichung von HRID 365763
[Br:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[CH3:7][O:8][CH:9](OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][CH2:2][C@@H:3]1[CH2:4][O:5][C@@H:7]([O:8][CH3:9])[O:6]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 208273-Bromo-1,2-propanediol

Produkt 1

HCID 86752979trans 4-(Bromomethyl)-2-methoxy-1,3-dioxolaneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-1,2-propanediol (6.0 g, 38.7 mmol) in benzene (90 mL) was added trimethylorthoformate (4.23 mL, 38.7 mmol, 1 eq.) and p-toluenesulfonic acid (pTSA, few crystals). The mixture was stirred for 20 hr at 85°-90° C., then cooled to room temperature and benzene was removed under reduced pressure. The crude material was obtained in 96% yield (7.26 g) as a mixture of cis and trans isomers in a 1:1 ratio.

Aufarbeitung

  1. custombenzene was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b1552334a7ac4abf8a0b3a375d1f32e8
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127540

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