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Chloromethylation of 1,3-benzodioxole in the presence of micellar catalysts.
Yingyong Huaxue (2000), 17(5), 563-565.
CODEN: YIHUED ISSN: 1000-0518. Journal written in Chinese.
Abstract
1,3-Benzodioxole was monochloromethylated directly by aq. formaldehyde and hydrogen chloride gas in CCl4 in the presence of quaternary ammonium salts: c16H33(CH3)3NX (X = Br, Cl), C12H25(CH3)3NCl, C12H25(CH3)2(C6H5CH2)NCl and (C4H9)4NBr. With hexadecyltrimethylammonium bromide at temp. 60°-65° for 15 h of reaction, 1,3-benzodioxole was converted to piperonyl chloride with conversion >98% and selectivity up to 97%. The method has advantages of high selectivity, high conversion, negligible byproducts and easy workup of the mail product.
a,a-Dimethyl-3,4-methylenedioxyhydrocinnamic aldehyde and flavoring materials containing the compound.
Sotoguchi, Tsukasa; Yamamoto, Takeshi. (Takasago Perfumery Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho (1989), 8 pp. CODEN: JKXXAF JP 01022868 A2 19890125 Heisei.
Patent written in Japanese.
Abstract
Flavoring materials contain the title compd. (I). I, which has strong and continuous floral fragrance, is stable and useful for various uses, e. g. cosmetics, hair prepns., soaps, detergents, drugs, etc. Treatment of 366 g methylenedioxybenzene with 99 g paraformaldehyde in MePh with feeding HCl at 25-35° for 4 h gave 423.6 g crude 3,4-methylenedioxybenzyl chloride, which was treated with 173 g isobutyraldehyde in the presence of NaOH and Bu4NI in H2O-MePh at 65° for 7 h to afford 481 g crude I. Pure I (212 g) was obtained after distn. A white soap flavored with 1% I was stored in a sealed container at 50° for 30 days to show no change of the flavor or discoloration of the soap, whereas change of flavor and yellowish discoloration were obsd. when a-methyl-3,4-methylenedioxyhydrocinnamic aldehyde was used instead of I.
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