Hydroxypropylation

Journal of Organic Chemistry

Volumn 37, Issue 12, 1972, Pages 1947-1950

  Eaton, Philip E ^a   Cooper, Gaey F ^a   Johnson, Richard C ^a   Mueller, Richard H ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001673971     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00977a019     Document Type: Article

References (18)

1. H. Erlenmeyer and R. Marbet, Helv. Chim. Acta, 29, 1946 (1946). See also.
2. M. S. Kharasch and O. Reinmuth, “Grignard Reactions of Non-metallic Substances,” Prentice-Hall, Englewood Cliffs, N. J., 1954, p 36, and references cited therein.
3. L. I. Smith and J. A. Sprung, U. S. Patent 2, 421, 090; cf.
4. Chem. Abstr., 41, 5543 (1947).
5. W. R. Renfrew, D. Oakes, C. Laver, and T. A. Walter, J. Org. Chem., 26, 935 (1961).
6. S. Chladek and J. Smrt, Chem. Ind. (London), 1719 (1964).
7. W. A. Mosher and D. M. Preiss, J. Amer. Chem. Soc, 75, 5605 (1953).
8. C. Raí and S. Dev, J. Indian Chem. Soc, 34, 178 (1957), and references cited therein
9. P. E. Eaton and R. H. Mueller, J. Amer. Chem. Soc, 94, 1014 (1972).
10. This convenient designation represents only the stoichiometry of the reaction; see E. J. Corey and G. H. Posner, J. Amer. Chem. Soc, 90, 5615 (1968), footnote 7.
11. H. O. House, W. L. Respess, and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966), and references cited therein give other examples using different systems.
12. H. Stetter, I. KrÜger-Hansen, and M. Rizk, Chem. Ber., 94, 2702 (1961).
13. J. P. Schroeder, D. C. Schroeder, J. Hardin, and J. K. Marshall, J. Org. Chem., 34, 3332 (1969).
14. A. I. Meyers, I. R. Politzer, B. K. Bandlish, and G. R. Malone, J. Amer. Chem. Soc., 91, 5886 (1969).
15. J. J. Ritter and E. -J. Tillmans, J. Org. Ckem., 22, 839 (1957).
16. G. BÜchi and H. WÜest, J. Org. Ckem., 34, 1122 (1969).
17. “Usual work-up” is shorthand for extraction with the named solvent, drying the extract with sodium sulfate, filtration, and concentration under vacumm on a rotary evaporator.
18. G. B. Kauffman and L. A. Teter, Inorg. Syn., 7, 9 (1963). The purified cuprous iodide should be finely powdered before use.