4,4-Bis(hydroxymethyl)-2-phenyl-2-oxazoline

Round 1

Reviewer 1 Report

The manuscript by Sara Hajib reports the synthesis of 4,4-bis(hydroxymethyl)-2-phenyl-2-oxazoline. This compound, as the authors indicate in the text, is well known from the literature. Reaxys search results in five different methods of preparation for the title compound ([European Journal of Organic Chemistry, 2003, # 22, p. 4387 - 4391]; [Tetrahedron Letters, 1981, vol. 22, # 45, p. 4471 - 4474]; [Journal of the American Chemical Society, 1945, vol. 67, p. 1069]; [Tetrahedron, 1993, vol. 49, # 41, p. 9353 - 9372]; [US2556791, 1945]). The method proposed by the authors is very similar to the one published in [Journal of the American Chemical Society, 1945, vol. 67, p. 1069], and the yield reported in the manuscript (85 %) is even lower than in the literature procedure (89-94 %). X-ray crystal structure determination is routine and alone cannot justify the publication in Molbank.

Author Response

Dear Reviewer

All the authors thank you very much for the review of our manuscript entitled: “ 4,4‐bis(hydroxymethyl)‐2‐phenyl‐2‐oxazoline”, ID data-911298.

We know that the compound subject of the structural determination is a commercial product whose synthesis is already described in the literature. The references you give in your comment have already been added in the bibliography section of our article : refs. : 18, 19, 20, 24). This is why we have submitted our paper to the structure determination section and not to the organic chemistry section. The major new part of this work is the structure determination. The structure of compound was characterized for the first time by a single‐crystal X‐ray structure determination and found it to have one independent molecule per asymmetric unit. In  the molecular packing, supramolecular dimers are formed mediated by C‐H…O, C‐H…N, O‐H…N, and O‐H…C hydrogen bonds. The compound was further established through 2D NMR spectroscopy, something that has not been done before.

So, we made some clarifications and changes ; and added additional information to further support the interest in publishing this paper for literature.  Please, check you the changes in the text of the revised version of our manuscript.

Author Response File: Author Response.docx

Reviewer 2 Report

From a synthetic point of view, the manuscript is not original but, to the best of my knowledge, a complete characterization and X-ray analysis of this molecule has never done. So I think the manuscript may be publishable after a minor revision.

Suggestions:

Authors should add the following reference as an alternative synthetic method: EurJOC 2003,(22),4387.

Line 32: "It was obtained" instead of "it's obtained"

Line 98: "was filtered" instead of "is filtered"

Author Response

Dear reviewer

All the Authors thank you for your efforts aimed to improve the quality of our manuscript.

Please find attached the revised version of the manuscript “ 4,4‐bis(hydroxymethyl)‐2‐phenyl‐2‐oxazoline”, ID data-911298. Your suggestions have been taken into account for the revision of the article

1. Authors should add the following reference as an alternative synthetic method: EurJOC 2003,(22),4387.

We added the reference ([EurJOC 2003, (22), 4387]) in the manuscript as ref. 24

2. Line 32: "It was obtained" instead of "it's obtained"

Correction done

3. Line 98: "was filtered" instead of "is filtered"

Correction done

Author Response File: Author Response.docx

Reviewer 3 Report

Alami and colleagues report the resynthesis of 4,4-bis(hydroxymethyl)-2-phenyl-2-oxazoline. The title compound is well-known and physical properties exist in literature. In addition, the resynthesis has been performed using conventional method as claimed by the authors. Besides, no novel studies has been done in this report that would be useful to the community. The resynthesized compound has been well characterized by the author and their discussion is consistent with the structure. However, the authors did not rationalize the need or value this manuscript will add to the literature other than mere characterization data. I would recommend the author to discuss early in the manuscript why this article should be published and if this report add anything that is not already present in the literature.

Please consider the following issues in the revised version:

1. 1H NMR in DMSO-d₆ would be more informative. In that case all protons would be observed including the hydroxyl protons. Besides, same data can be used both in Figure 1 and Table 1. 
2. page 4, lines 100-102: No need to specify decimal points in NMR frequency, 300 MHz and 75 MHz is fine (the same should be done everywhere). Acetone should be acetone-d₆; MeOD should be CD₃OD.

Author Response

Dear Reviewer

All the Authors thank you for your efforts aimed to improve the quality of our manuscript.

Authors acknowledge you comments because we think that help us to improve this paper.

So, as you recommended, we made some clarifications and changes ; and added additional information to further support the interest in publishing this paper for literature.  Please, check you the changes in the text of the revised version of the manuscript “ 4,4‐bis(hydroxymethyl)‐2‐phenyl‐2‐oxazoline”, ID data-911298.

The ¹H NMR spectrum of the title compound was carried out in CD₃OD and not in DMSO-d6. For this reason, we have noted the absence of the signals of the protons of the two alcohol functions.

We deleted the decimal points in NMR frequency, and we rectified the names of solvents; acetone-d6 and CD₃OD.

Author Response File: Author Response.docx

Round 2

Reviewer 1 Report

The authors have revised the manuscript and now place the accent on the new crystal structure determination, which can be considered as fitting the scope of the Journal.

Reviewer 3 Report

The authors have addressed the issues. I recommend publication.