A selective method for the preparation of aliphatic methyl esters in the presence of aromatic carboxylic acids

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8563-8566

  Rodriguez A ^a   Nomen, M ^a   Spur, B W ^a   Godfroid, J J ^b  

^a UMDNJ School of Osteopathic Medicine   (United States)

^b Laboratoire de Pharmacochimie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC CARBOXYLIC ACID METHYL ESTER DERIVATIVE; AROMATIC CARBOXYLIC ACID; HYDROCHLORIC ACID; METHANOL; PROPANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0032548053     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01958-3     Document Type: Article

References (10)

1. 1. Ogliaruso, M.A.; Wolfe, J.F. Synthesis of Carboxylic Acids, Esters And Their Derivatives; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons, Inc.: New York, 1991, 145-148.
2. 2. Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis 2ed. John Wiley & Sons, Inc., 1991, 224-276.
3. 3. Ram, R.N.; Charles, I. Tetrahedron 1997, 53, 7335-7340.
4. 4. Banerjee, A.; Adak, M.M.; Das, S.; Banerjee, S.; Sengupta, S. J. Indian Chem. Soc. 1987, 64, 34-37.
5. 5. Ogawa, T.; Hikasa, T.; Ikegami, T.; Ono, N.; Suzuki, H. J. Chem. Soc. Perkin Trans. 1 1994, 23, 3473-3478.
6. 6. Blossey, E.C.; Turner, L.M.; Neekers, D.C. Tetrahedron Lett. 1973, 1823.
7. 7. Nakao, R., Oka, K.; Fukumoto, T. Bull. Chem. Soc. Jpn. 1981, 54, 1267-1268.
8. 8. Brook, M.A.; Chan, T.H. Synthesis 1983, 201-203.
9. 9. A representative experimental procedure is as follows: 0.38 ml (3.0 mmol) of trimethylsilyl chloride were added to a stirred suspension of 5.4 g (30.0 mmol) of homophthalic acid (Aldrich Chemical Company, Inc.) in 48 ml of 2,2-dimethoxypropane and 12 ml of methanol The mixture was stirred for 18 hours at room temperature. Concentration under reduced pressure afforded crude monoester. Analysis by NMR showed the presence of 1.7% of diester. The crude product was purified by recrystallisation from ethyl acetate mp= 96-97 °C (Lit. mp 98 °C) (95% yield).
10. 13C-NMR, FT-IR, were obtained for all compounds.