Citric Acid → 2-[2-(Dodecyloxy)-2-oxoethyl]-2-hydroxybutanedioic acid

HRID 1679809Notes

Reaction equation

HRID 1679809 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][C:3]([CH2:8][C:9]([OH:11])=[O:10])([C:5]([OH:7])=[O:6])[OH:4].[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[CH2:25]([O:10][C:9](=[O:11])[CH2:8][C:3]([CH2:2][C:1]([OH:13])=[O:12])([C:5]([OH:7])=[O:6])[OH:4])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 6101p-Toluenesulfonic acidHCID 81931-Dodecanol

Product 1

HCID 130085892-[2-(Dodecyloxy)-2-oxoethyl]-2-hydroxybutanedioic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A blend of citric acid (63 grams, 0.3 mole), dodecyl alcohol (55.8 grams, 0.31 mole), p-toluene sulfonic acid (0.1 gram, 0.6 mole) and 300 ml. of dioxane was refluxed for 72 hours, passing the condensed vapor through 4A molecular sieve. The dioxane solvent was then evaporated under reduced pressure (30 mm.) to a 150 gram residue. This mixture was diluted with 200 ml. of toluene and the reaction mixture subsequently stripped to 60° C. at 5 mm. pressure. The residue was an amber oil which solidified to a cream colored soft solid, weight 106.6 grams (Theory 108 grams).

Workup

  1. customThe dioxane solvent was then evaporated under reduced pressure (30 mm.) to a 150 gram residue
  2. additionThis mixture was diluted with 200 ml
  3. customsubsequently stripped to 60° C. at 5 mm

Sources & evidence

ORD record
ord-a245c73507f34b3c9c7c843f1a9816b0
Source dataset
uspto-grants-1981_06
Patent number
US04271032

Reaction notes

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