By Sidney M. Cantor
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53 53 79 34 R. A. LAIDLAW AND E. G. V. PERCNAL T o m VI The Methyl E h e of cRhamnoee Subetance 2-Methyl-crhamnose -, methyl pyranoside 3-Methyl-crhamnose -, phenylosasone Melting point, "C. 3 - 1 8 . 3+ +44. 6 - 67 +36 76-78 162-166 -160-+ - 111 40-41 177 100 +14 62 02 80 02 62 02 02 02 69, 63, 04 63 03 69 66 66 06 -116 - - 1 3 0 4 -78 - (82) F. G. Young and R. C. Elderfield, J . Org. , 7, 241 (1942). (83) J. Avery and E. L. Hirst, J . Chm. , 2466 (1929). 65, 66 66 26, 67 36 83 80 36 35 METHYL ETHERS TABLEI VII The Methyl Ethers of ~-Fucose Substance ZMethyl-D-fucose -, methyl 3,4isopropylidenepyranosidea %Methyl-D-fucoae -, phenyloeszone -, methyl a-pyranoside methyl 8-pyranoside %Methyl-D-fuconicacid -, lactone -, 2,3,4-Trimethyl-~-fucose -, hydrate (a-anomer) -, anilide -, methyl 8-pyranoside Melting point, "C.
Am. Chem. , 79, 4658 (1951). (9) Unpublished data from studies of levoglucosan production, by I. A. Wolff, 5). W. Olds and G. E. Hilbert at the Northern Regional Research Laboratory. 40 R. J. DIMLER mother liquor left after crystallization of levoglucosen from the pyrolyzate was acetylated with acetic anhydride in the presence of pyridine and the acetate mixture distilled under reduced pressure. 1 mm. were discarded. From the distilled acetate some levoglucosan triacetate was removed by crystallization from 2-propanol.
The use of an electrically heated jacket instead of a burner for heating the flask resulted in better control of the reaction. In addition, the dextrorotation of a solution of the sirupy distillate was about twice that reported by Hann and Hudson for their product from the same weight of galactose. The acetonation was carried out on the entire distillate, thereby avoiding the steps of decolorization, concentration and acetone extraction. The acetonated mixture waa extracted directly with chloroform, care being taken to minimize the possibility of hydrolysis of the 3,4-isopropylidene-D-galactosan < 1,5>8 < 1,6> while in the presence of the residual sirups.