P-cymenesulphonyl chloride: A bio-based activating group and protecting group for greener organic synthesis

TY - JOUR

T1 - P-cymenesulphonyl chloride

T2 - A bio-based activating group and protecting group for greener organic synthesis

AU - Farmer, Thomas J.

AU - Clark, James H.

AU - Gothe, Maite L.

AU - Macquarrie, Duncan J.

AU - Sherwood, James

PY - 2015/9/1

Y1 - 2015/9/1

N2 - A bio-derived protecting/activating group has been synthesized by introducing a sulphonyl chloride group to the aromatic ring of p-cymene derived from citrus peel waste. The resulting p-cymenesulphonyl chloride was evaluated as an activating group by reacting with 1-octanol, 2-octanol, phenol and piperidine, and further reactions of the activated alcohols. The comparison to tosyl chloride demonstrates that the bio-based alternative can be effectively utilized as a direct replacement for the current fossil derived equivalent.

AB - A bio-derived protecting/activating group has been synthesized by introducing a sulphonyl chloride group to the aromatic ring of p-cymene derived from citrus peel waste. The resulting p-cymenesulphonyl chloride was evaluated as an activating group by reacting with 1-octanol, 2-octanol, phenol and piperidine, and further reactions of the activated alcohols. The comparison to tosyl chloride demonstrates that the bio-based alternative can be effectively utilized as a direct replacement for the current fossil derived equivalent.

KW - Activating group

KW - Citrus waste

KW - P-cymene

KW - Protecting group

KW - Sulphonyl chloride

UR - http://www.scopus.com/inward/record.url?scp=84941585289&partnerID=8YFLogxK

U2 - 10.5935/0103-5053.20150169

DO - 10.5935/0103-5053.20150169

M3 - Article

AN - SCOPUS:84941585289

SN - 0103-5053

VL - 26

SP - 1914

EP - 1919

JO - Journal of the Brazilian Chemical Society

JF - Journal of the Brazilian Chemical Society

IS - 9

ER -