Exceptionally facile conversion of carboxylic acid salts to aldehydes by reductive oxidation with borane and pyridinium chlorochromate

Bulletin of the Korean Chemical Society

Volumn 22, Issue 3, 2001, Pages 325-326

  Cha, Jin Soon ^a   Park, Jae Hyung ^a   Lee, Dae Yon ^a  

^a Yeungnam University   (South Korea)

Author keywords

Aldehyde synthesis; Borane; Carboxylic acid salts; PCC; Reductive oxidation

Indexed keywords

ALDEHYDE; BORANE DERIVATIVE; CARBOXYLIC ACID SALT; CHROMIC ACID; PYRIDINIUM DERIVATIVE;

ANALYTIC METHOD; CHEMICAL REACTION; COMPLEX FORMATION; NOTE; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0000757067     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Note

References (16)

1. Cha, J. S.; Kim, J. E.; Lee. K.W. J. Org. Chem. 1987, 52, 5030.
2. Cha, J. S.; Oh, S. Y.; Lee, K. W.; Yoon, M. S.; Lee, J. C. Hetetocycles 1988, 27, 1595.
3. (a) Brown, H. C.; Rao, C. G.; Kulkarni, S. U. Synthesis 1979, 704.
4. (b) Cha, J. S.; Kim, J. M.; Kwon, O. O.; Lee, J. C. Bull. Korean Chem. Soc. 1998, 19, 1301.
5. (c) Cha, J. S.; Chun, J. H.; Kim, J. M.; Kwon, O. O.; Kwon, S. Y.; Lee, J. C. Bull. Korean Chem. Soc. 1999, 20, 400.
6. (d) Cha, J. S.; Lee, D. Y.; Kim, J. M. Org. Prep. Proced. Int. 1999, 31, 694.
7. (a) Cha, J. S.; Kim, J. M.; Chun, J. H.; Kwon, O. O.; Kwon, S. Y.; Cho, S. D. Bull. Korean Chem. Soc. 1998, 19, 1301.
8. (b) Cha, J. S.; Chun, J. H.; Kim, J. M.; Lee, D. Y.; Cho, S. D. Bull. Korean Chem. Soc. 1999, 20, 1373.
9. (a) Cha, J. S.; Kim, J. M.; Chun, J. H.; Kwon, O. O.; Kwon, S. Y.; Han, S. W. Org. Prep. Proced. Int. 1999, 31, 204.
10. (b) Cha, J. S.; Chun, J. H. Bull. Korean Chem. Soc. 2000, 21, 375.
11. Yoon, N. M.; Pak, C. S.; Brown, H. C.; Krishnamurthy, S.; Stocky, T. P. J. Org. Chem. 1973, 38, 2786.
12. 4 in THF.
13. The solid salt disappeared and the slurry became clearer.
14. In the case of Na salts of aliphatic carboxylic acid, the temperature should be maintained below 15 °C; the yields of aldehydes drops significantly above that temperature.
15. The Na salts requires 6 hrs for the complete evolution of methane.
16. The oxidation requires 3 hrs under reflux or 12 hrs at room temperature for the aliphatic series; 6 hrs at room temperature for the aromatic series.