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It is known that diethyl and dibutyl ethers are good solvents for Grignards, it has been also found that diisopropyl ether does not work. I have never seen dipropyl being discussed.

Edit: For clarity, ISOpropyl does not work very well, I want to know whether n-propyl would work.

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  • $\begingroup$ It probably would work s a solvent, but di-isopropyl ether is more reactive than $n$- alkyl ethers to peroxide formation, which is an explosion hazard. Also when not exploding the peroxide function may also react with the Grignard reagent. $\endgroup$ Commented 2 days ago
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    $\begingroup$ Wait, di(n-propyl)ether or di-isopropyl? It pretty much impossible that the linear isomer "does not work". $\endgroup$
    – Mithoron
    Commented 2 days ago
  • $\begingroup$ Not discussed in the literature probably because it is more expensive than diethyl ether and offers no significant advantages over that or di-n-butyl ether. I don't see why it would not work though. $\endgroup$
    – Waylander
    Commented 2 days ago

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A study was conducted in 1931 on this very subject. The full text was not available in Chemical Abstracts but the names of the authors, institution and abstract were provided. (https://scifinder-n.cas.org/search/all/6668add88eab8e3392cf2506). The results are variable. Attempts to employ alkyl iodides gave poor results while alkyl bromides fared better.

Diisopropyl ether as a solvent in the Grignard reaction By: Rathmann, F. H.; Leighty, J. A. Transactions of the Illinois State Academy of Science (1931), 24, 312-5 |

On account of its cheapness and low volatility, (iso-Pr)2O would seem a desirable substitute for Et2O in the preparation of Grignard reagents. However, it was found less satisfactory in the following cases: MeI and Mg failed to react in (iso-Pr)2O in the presence of an I2 crystal. EtI and Mg reacted well at first, but the Mg was soon coated over with a white solid. The yield was 22.5% against 86% in Et2O. MgEtBr was prepared in Et2O, (iso-Pr)2O and Bu2O media, giving yields of 75-88, 67.5 and 74-5%, resp. The reaction of iso-AmI on Mg in (iso-Pr)2O was stopped by a coating on the metal. PhBr and Mg in (iso-Pr)2O in the presence of an I2 crystal gave a yield of only 34%, although stirred mechanically under a reflux condenser for 3 hrs. Yields of Me2EtCOH and EtPhCHOH in (iso-Pr)2O were less than half the yields in Et2O.

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