Regioselective acetylation of 4-t-butylcyclohexanol in presence of β-cyclodextrin and its derivatives

Pattekhan, H. H. and Divakar, S. (2002) Regioselective acetylation of 4-t-butylcyclohexanol in presence of β-cyclodextrin and its derivatives. Journal of Molecular Catalysis A: Chemical, 184. pp. 79-83.

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Abstract

Regioselective acetylation of 4-t-butylcyclohexanol (I) in the presence of Regioselective acetylation of 4-t-butylcyclohexanol (I) in the presence of Regioselective acetylation of 4-t-butylcyclohexanol (I) in the presence of β-CD,DM β-CD,HPβ-CD and β-CD-polymerwas carried out with 10–20 times excess acetic anhydride. At 1:10 ratio I and acetic anhydride, the control showed good amount of conversion (99.0%) to 4-t-butylcyclohexyl acetate (II) with a trans/cis ratio of 3.48 with very little unreacted alcohols present (trans/cis ratio 2.5). With increase in concentration of β-CD, although the ester yield was less than the control, the trans/cis ratio increased steadily from 3.46 for 1:0.1 (yield 57.7%) to 5.49 for 1:1 eq.(yield 74.4%) of I to β-CD. However, the trans ester yield was comparable to the control (76.9%) in the presence of 1 eq. of β-CD. The results indicated selectivity in esterification between the trans and cis alcohols due to inclusion inside β-CD cavity.-CD,DMβ-CD,HPβ-CD and β-CD-polymerwas carried out with 10–20 times excess acetic anhydride. At 1:10 ratio I and acetic anhydride, the control showed good amount of conversion (99.0%) to 4-t-butylcyclohexyl acetate (II) with a trans/cis ratio of 3.48 with very little unreacted alcohols present (trans/cis ratio 2.5). With increase in concentration of β-CD, although the ester yield was less than the control, the trans/cis ratio increased steadily from 3.46 for 1:0.1 (yield 57.7%) to 5.49 for 1:1 eq.(yield 74.4%) of I to β-CD. However, the trans ester yield was comparable to the control (76.9%) in the presence of 1 eq. of β-CD. The results indicated selectivity in esterification between the trans and cis alcohols due to inclusion inside β-CD cavity.-CD,DMβ-CD,HPβ-CD and β-CD-polymer was carried out with 10–20 times excess acetic anhydride. At 1:10 ratio I and acetic anhydride, the control showed good amount of conversion (99.0%) to 4-t-butylcyclohexyl acetate (II) with a trans/cis ratio of 3.48 with very little unreacted alcohols present (trans/cis ratio 2.5). With increase in concentration of β-CD, although the ester yield was less than the control, the trans/cis ratio increased steadily from 3.46 for 1:0.1 (yield 57.7%) to 5.49 for 1:1 eq.(yield 74.4%) of I to β-CD. However, the trans ester yield was comparable to the control (76.9%) in the presence of 1 eq. of β-CD. The results indicated selectivity in esterification between the trans and cis alcohols due to inclusion inside β-CD cavity.

Item Type:	Article
Uncontrolled Keywords:	β-Cyclodextrin; Regioselectivity; 4-t-Butylcyclohexanol; 4-t-Butylcyclohexyl acetate; Trans/cis ratio
Subjects:	500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 12 Aromatic Chemistry
Divisions:	Fermentation Technology and Bioengineering
Depositing User:	Food Sci. & Technol. Information Services
Date Deposited:	22 Jun 2007 03:53
Last Modified:	05 Oct 2018 06:16
URI:	http://ir.cftri.res.in/id/eprint/1222

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