S Y N T H E S I S OF FURAN A C I D S

(UDC 542.91+547.72)

V. G. G l u k h o v t s e v and S. V. Z a k h a r o v a

N. D. Zelinskii Institute for Organic Chemistry, Academy of Sciences, USSR Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 945-946, May, 1964 Original article submitted February 12, 1964

Until recently only multiple step synthetic methods were known for furan acids [1-3]. We found that these syntheses can be accomplished in one step. Thus, for example, 2-methylfuran and 2-(2'-earbomethoxyethyl)furan will react at ~ 25 ~ with acrylic acid in the presence of H2SO 4 according to the scheme:

r~=so~n R - - ' [ ~ o J + C H 2 = C H C O O H --I~o.~CHzCH~COOH R--CII3: CH~CII~.COOCH.~

Thus, the corresponding 2-methyl-5-(2'-carboxyethyl)furan boiling at 108" (3.5 ram), m.p. 57-57.5*was obtained. Found: C 62.20; 62.24; H 6.45; 6.48~ acid number was 278. CsH10Os. Calculated: C 62.32, H 6.54%. Acid number 272. The literature data [1] are m.p. 57-57.5* and for 2-(2'-carbomethoxyethyl)-5-(2'-carboxyethyl)furan boiling at 158" (3 ram), m.p. 48*. Found: C 58.52, 58.30; H 6.23,6.13%. Acid number 181. CgHtzO s. Calculated: C 58.38, H 6.24~ Acid number 185. Constants for the latter compound were previously described [4]: 2,5-bis(2'- carbomethoxyethyl)furan was obtained by esterifying [3] 2-(2'-carbomethoxyethyl-5-(2'-carboxyethyl)furan and boiled at 110" (2 ram): n 1 1.4790, d4 z~ 1.1420. Found: C 59.78; 59,52; H 6.55; 6.5007 o. CmH10Os. Calculated: C 59.98; H 6.6 ~r/0. Structures of the compounds we obtained were confirmed by IR spectral data.

L I T E R A T U R E C I T E D

1. D . A . H . Taylor, I. Chem. Soc., 1959, 2767. 2. S.M. Sherlin, A. Ya. Berlin, T. A. Serebryannikova, and F. E. Rabinovich, Zh. obshch, khimii,_8, 7 (1938). 3. S.R. Robinson and W. M. Todd, J. Chem. Soc., 1939, 1743. 4. Y. Asahina and A. Fujita, Chem. Zentralblatt, 1922, III, 712.

SYNTHESIS OF 2-ALKYL-I,2-OXABOROLANES

(UDC 547.244)

B. M. M i k h a i l o v a n d V. A. D o r o k h o v

N. D. Zelinskii Institute for Organic Chemistry, Academy of Sciences, USSR Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, p. 946, May, 1964 Original article submitted February 20, 1964

We found that the allyl ester of di-n-butylboric acid in the presence of tri-n-butylboron is readily converted above 150 ~ to 2-n-butyl-l ,2-oxaborolane (I) by cleavage of butytene.

(n-CaHg)~ BOCH2CH~, ---- CH2

0- CH2

l s o ~ + n-C~HgB (i) \ CHz--CH2

+ C4Hs

887