DOI: 10.1246/bcsj.55.2186. The Preparation of Optically Pure 3-Hydroxyalkanoic Acid. The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVII.

The Preparation of Optically Pure 3-Hydroxyalkanoic Acid. The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVII.

10.1246/bcsj.55.2186

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract The enantioface-differentiating hydrogenation of methyl 3-oxoalkanoate (CH3(CH2)nCOCH2COOCH3, n=0, 6, 8, 10, 12) over the (R,R)-tartaric acid–NaBr–modified Raney nickel catalyst ((R,R)-TA–NaBr–MRNi) gave methyl (R)-3-hydroxyalkanoate (CH3(CH2)nCH(OH)CH2COOCH3, n=0, 6, 8, 10, 12) in an average optical yield of 85%. After the methyl ester had been converted to dicyclohexylammonium salt of 3-hydroxyalkanoic acid, the salt was recrystallized three times from acetonitrile and then treated with acid to give optically pure (R)-3-hydroxyalkanoic acid (CH3(CH2)nCH(OH)CH2COOH, n=0, 6, 8, 10, 12) in a reasonable yield. From the hydrogenation product with (S,S)-TA–NaBr–MRNi, optically pure (S)-3-hydroxyalkanoic acid was obtained by the same process as above.

Bibliography

Nakahata, M., Imaida, M., Ozaki, H., Harada, T., & Tai, A. (1982). The Preparation of Optically Pure 3-Hydroxyalkanoic Acid. The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVII. Bulletin of the Chemical Society of Japan, 55(7), 2186â2189.

Authors 5

Masaaki Nakahata (first)
Motomasa Imaida (additional)
Hiroshi Ozaki (additional)
Tadao Harada (additional)
Akira Tai (additional)

References 16 Referenced 80

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10.1126/science.155.3758.52
10.1021/jo00868a022
10.3891/acta.chem.scand.09-0866
{'key': '2024011802311908000_r7'}
{'key': '2024011802311908000_r8'}
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10.1021/jo00404a066
{'key': '2024011802311908000_r11'}
10.1021/jo01316a039
10.1021/ja00811a023
10.1246/bcsj.54.2323
10.1021/ja01101a007
{'key': '2024011802311908000_r16'}

Dates

Type	When
Created	19 years, 1 month ago (July 25, 2006, 9:06 p.m.)
Deposited	1 year, 7 months ago (Jan. 17, 2024, 9:31 p.m.)
Indexed	2 months, 2 weeks ago (June 24, 2025, 3:47 a.m.)
Issued	43 years, 2 months ago (July 1, 1982)
Published	43 years, 2 months ago (July 1, 1982)
Published Online	19 years, 2 months ago (June 27, 2006)
Published Print	43 years, 2 months ago (July 1, 1982)

Funders 0

None

BibTeX

@article{Nakahata_1982, title={The Preparation of Optically Pure 3-Hydroxyalkanoic Acid. The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVII.}, volume={55}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.55.2186}, DOI={10.1246/bcsj.55.2186}, number={7}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Nakahata, Masaaki and Imaida, Motomasa and Ozaki, Hiroshi and Harada, Tadao and Tai, Akira}, year={1982}, month=jul, pages={2186–2189} }

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