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. Author manuscript; available in PMC: 2010 Jan 1.
Published in final edited form as: Synth Commun. 2009 Jan 1;39(9):5193–5196. doi: 10.1080/00397910802542044

Table 1.

Summary of Conrad-Limpach reaction results with selected solvents.

Solvent a
A B C D E F G H I J K
Solvent
BP (°C) b 		200 213 230 240 222 230 208 190 213 257 253
Cost
($/L)c 		26 35 340 340 20 22 21 45 32 122 30
Yield 25% 34% 65% 66% 51% n/ad 44% n/ae 54% 65% 65%
Product
color		 light
brown		 dark
brown		 black black light
brown		 n/ad dark
brown		 n/ae dark
brown		 light
brown		 light
brown
a

A , m ethyl benzoate; B , ethyl benzoate; C , propyl benzoate; D , isobutyl benzoate; E , 2-nitrotoluene; F , 1,4-butanediol; G , tetrahydronaphthalene; H , decahydronaphthalene; I, 1,2,4-trichlorobenzene; J, D ow therm A ; K , 2,6-di-tert-butylphenol.

b

Obtained from Lange’s Handbook, 14 thedition.

c

Obtained from Aldrich catalog, 2007 -2008 edition.

d

Reaction with 1,4-butanediol did not produce any product.

e

Reaction with decahydronaphthalene yielded only non -cyclized enam ine product.