p-Toluenesulfonic acid → 2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate

HRID 858264Notes

Reaction equation

[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](O)(=[O:18])=[O:17])=[CH:12][CH:11]=1.Cl.C(OCC)C>N1C=CC=CC=1>[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([O:8][CH2:7][CH:5]2[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5.29 g (40.0 mmol) of (2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (Solketal®) and 10 ml of pyridine are introduced into a round-bottomed flask under an argon atmosphere. The mixture is cooled to 0° C., 8.39 g (44.0 mmol) of para-toluenesulphonic acid are added and the mixture is stirred for sixteen hours at room temperature. The reaction medium is poured into a 1N HCl/ethyl ether mixture, extracted with ethyl ether, washed with water, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with dichloromethane. After evaporation of the solvents, 9.70 g (85%) of the expected product are collected in the form of yellow crystals with a melting point of 45–47° C.

Workup

extractionextracted with ethyl ether
washwashed with water
dry with materialdried over magnesium sulphate
customevaporated
customThe residue obtained
customis purified by chromatography on a column of silica
washeluted with dichloromethane
customAfter evaporation of the solvents, 9.70 g (85%) of the expected product
customare collected in the form of yellow crystals with a melting point of 45–47° C.

Sources & evidence

ORD record: ord-7be99c9a743b40e6abab6aeaf0ed66d4
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148245B2

Reaction notes

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