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

HRID 1679808

Reaction equation

HRID 1679808 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

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 81931-DodecanolHCID 155601,2,3,4-Butanetetracarboxylic acidHCID 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.

Workup

  1. temperatureto reflux with the vapor condensate
  2. customto remove water
  3. customformed during the reaction
  4. temperatureAfter 48 hours reflux
  5. customthe dioxane solution was removed

Sources & evidence

ORD record
ord-1ef41439e74047c69765127a3829d895
Source dataset
uspto-grants-1981_06
Patent number
US04271032

Linked notes

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