p-Toluenesulfonic acid → 1,2,3,4-Butane Tetracarboxylic Acid Monododecyl Ester

Reaction equation

[CH2:1]([C:14]([OH:16])=[O:15])[CH:2]([C:11]([OH:13])=[O:12])[CH:3]([C:8]([OH:10])=[O:9])[CH2:4][C:5]([OH:7])=[O:6].[CH2:17](O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCOCC1>>[CH2:28]([O:6][C:5]([CH2:4][CH:3]([C:8]([OH:10])=[O:9])[CH:2]([C:11]([OH:13])=[O:12])[CH2:1][C:14]([OH:16])=[O:15])=[O:7])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17]

Participants

Reactant 4

HCID 6101p-Toluenesulfonic acid

HCID 81931-Dodecanol

HCID 155601,2,3,4-Butanetetracarboxylic acid

HCID 312751,4-Dioxane

Product 1

HCID 178700661,2,3,4-Butane Tetracarboxylic Acid Monododecyl Ester

Procedure

A blend of 1,2,3,4-butane tetracarboxylic acid (28.5 g., 0.121 mole), dodecyl alcohol (21.8 grams, 0.118 mole), p-toluenesulfonic acid (0.1 gram, 0.6 mole) and 300 ml. (3.4 moles) of dioxane was placed in a Soxhlet apparatus containing 4A molecular sieve. The mixture was brought to reflux with the vapor condensate passing through the molecular sieve to remove water formed during the reaction. After 48 hours reflux, the dioxane solution was removed and stripped of solvent under reduced pressure (20 mm.). The residue (50 grams) showed the presence of both carboxylic acid and ester groups in the infrared.