Isoamyl (E)-3-(3,4-Dimethoxyphenyl)acrylate
Round 1
Reviewer 1 Report
Egar Pamela et al. presented a manuscript on isoamyl (E)-3-(3,4-dimethoxyphenyl)acrylate. Synthesis along with in vitro Sun Protection Factor (SPF) were described.
Although the preparation of (E)-3-(3,4-dimethoxyphenyl)acrylate was not reported. However, the condensation reaction by the same procedure was reported (Reference 12 in the manuscript and in DOI: 10.1246/cl.2002.286).
Some comments should be considered before the manuscript is accepted for publication.
(1) The authors can put the mechanism in the Supporting Information.
(2) If it is possible, you can put the NMR spectrum in the main text rather than in the Supporting Information
(3) In the NMR data, you should assign the NMR spectrum peaks with the molecule's H atoms.
(4) In the mass spectrum, we can see there are some extra highly intense peaks which are 579.1752, 279.1756, and 191.1122. You should assign them as well.
(5) The reaction was carried out on a small scale (0.31 g, 1.50 mmol). Is the reaction possible with a similar yield on a larger scale? Please share the information if you know.
(6) You did not mention whether the reaction was carried out with dry DCM or in the N2 atmosphere. Please mention them so that the readers will understand how sensitive the reaction is.
(7) As the reaction is based on the synthetic procedure of (E)-3-(3,4-dimethoxyphenyl, I would like to recommend writing the synthetic procedure in more detail, such as color changes, etc.
(8) The Rf value of the molecule by TLC must be mentioned.
(9) The font size in the Figures in the Supporting Information especially on the NMR spectrum, should be in larger fonts so that it would be easier for the readers to understand.
Author Response
Some comments should be considered before the manuscript is accepted for publication.
- The authors can put the mechanism in the Supporting Information.
Response: we have included in Figure S5 of the Supplementary Materials.
- If it is possible, you can put the NMR spectrum in the main text rather than in the Supporting Information
Response: the manuscript is a short note, therefore we prefer to put the NMR spectrum in the Supplementary Materials.
- In the NMR data, you should assign the NMR spectrum peaks with the molecule's H atoms.
Response: we have revised the manuscript.
(4) In the mass spectrum, we can see there are some extra highly intense peaks which are 579.1752, 279.1756, and 191.1122. You should assign them as well.
Response: we have assigned the peaks in Figure S4 of the Supplementary Materials.
- The reaction was carried out on a small scale (0.31 g, 1.50 mmol). Is the reaction possible with a similar yield on a larger scale? Please share the information if you know.
Response: we have carried out the reaction in larger scale (1.55g, 7.50 mmol), and the yield slightly reduced to 94%.
- You did not mention whether the reaction was carried out with dry DCM or in the N2 Please mention them so that the readers will understand how sensitive the reaction is.
Response: the reaction was carried in anhydrous DCM without inert condition.
- As the reaction is based on the synthetic procedure of (E)-3-(3,4-dimethoxyphenyl, I would like to recommend writing the synthetic procedure in more detail, such as color changes, etc.
Response: there was a color change at the beginning of the reaction from bright yellow to light yellow, then no color change until the end of the reaction.
- The Rf value of the molecule by TLC must be mentioned.
Response: we have revised the manuscript.
(9) The font size in the Figures in the Supporting Information especially on the NMR spectrum, should be in larger fonts so that it would be easier for the readers to understand.
Response: we have revised the manuscript.
Round 2
Reviewer 1 Report
Some comments should be considered before the manuscript is accepted for publication.
It is highly recommended that the author should make all the changes highlighted and mention page no. and line no. where the changes have been made.
They have addressed all the comments. However, I would like some minor changes to be made before the paper is accepted to be published.
- The authors can put the mechanism in the Supporting Information.
Response: we have included in Figure S5 of the Supplementary Materials.
The mechanism looks good. It would be helpful for the readers. You can refer them in the main text.
If it is possible, you can put the NMR spectrum in the main text rather than in the Supporting Information
Response: the manuscript is a short note, therefore we prefer to put the NMR spectrum in the Supplementary Materials.
That’s all right.
- In the NMR data, you should assign the NMR spectrum peaks with the molecule's H atoms.
Response: we have revised the manuscript.
Looks good.
(4) In the mass spectrum, we can see there are some extra highly intense peaks which are 579.1752, 279.1756, and 191.1122. You should assign them as well.
Looks good. You should mention them in the text where you mention the HRESIMS.
Response: we have assigned the peaks in Figure S4 of the Supplementary Materials.
- The reaction was carried out on a small scale (0.31 g, 1.50 mmol). Is the reaction possible with a similar yield on a larger scale? Please share the information if you know.
Response: we have carried out the reaction in larger scale (1.55g, 7.50 mmol), and the yield slightly reduced to 94%.
You should mention these in the manuscript. Yields of 94% and 95% are almost equal. Is not that?
- You did not mention whether the reaction was carried out with dry DCM or in the N2 Please mention them so that the readers will understand how sensitive the reaction is.
Response: the reaction was carried in anhydrous DCM without inert condition.
You should mention these in the manuscript in detail.
- As the reaction is based on the synthetic procedure of (E)-3-(3,4-dimethoxyphenyl, I would like to recommend writing the synthetic procedure in more detail, such as color changes, etc.
Response: there was a color change at the beginning of the reaction from bright yellow to light yellow, then no color change until the end of the reaction.
You should mention these in the manuscript.
- The Rf value of the molecule by TLC must be mentioned.
Response: we have revised the manuscript.
Looks good.
(9) The font size in the Figures in the Supporting Information especially on the NMR spectrum, should be in larger fonts so that it would be easier for the readers to understand.
Response: we have revised the manuscript.
Looks better. However, they could be improved.
Author Response
They have addressed all the comments. However, I would like some minor changes to be made before the paper is accepted to be published.
- The authors can put the mechanism in the Supporting Information.
Response: we have included in Figure S5 of the Supplementary Materials.
The mechanism looks good. It would be helpful for the readers. You can refer them in the main text.
Response: We have revised the manuscript.
If it is possible, you can put the NMR spectrum in the main text rather than in the Supporting Information
Response: the manuscript is a short note, therefore we prefer to put the NMR spectrum in the Supplementary Materials.
That’s all right.
- In the NMR data, you should assign the NMR spectrum peaks with the molecule's H atoms.
Response: we have revised the manuscript.
Looks good.
(4) In the mass spectrum, we can see there are some extra highly intense peaks which are 579.1752, 279.1756, and 191.1122. You should assign them as well.
Response: we have assigned the peaks in Figure S4 of the Supplementary Materials.
Looks good. You should mention them in the text where you mention the HRESIMS.
Response: We have revised the manuscript.
- The reaction was carried out on a small scale (0.31 g, 1.50 mmol). Is the reaction possible with a similar yield on a larger scale? Please share the information if you know.
Response: we have carried out the reaction in larger scale (1.55g, 7.50 mmol), and the yield slightly reduced to 94%.
You should mention these in the manuscript. Yields of 94% and 95% are almost equal. Is not that?
Response: We have revised the manuscript.
- You did not mention whether the reaction was carried out with dry DCM or in the N2 Please mention them so that the readers will understand how sensitive the reaction is.
Response: the reaction was carried in anhydrous DCM without inert condition.
You should mention these in the manuscript in detail.
Response: We have revised the manuscript.
- As the reaction is based on the synthetic procedure of (E)-3-(3,4-dimethoxyphenyl, I would like to recommend writing the synthetic procedure in more detail, such as color changes, etc.
Response: there was a color change at the beginning of the reaction from bright yellow to light yellow, then no color change until the end of the reaction.
You should mention these in the manuscript.
Response: We have revised the manuscript.
- The Rf value of the molecule by TLC must be mentioned.
Response: we have revised the manuscript.
Looks good.
(9) The font size in the Figures in the Supporting Information especially on the NMR spectrum, should be in larger fonts so that it would be easier for the readers to understand.
Response: we have revised the manuscript.
Looks better. However, they could be improved.
Response: We have revised the supplementary materials.
