Adipic Acid → HCID 86746458, compound

HRID 1645780Notes

Reaction equation

HRID 1645780 reaction equation
[CH:1]([CH:15]1[CH2:20][C:19](=[O:21])[O:18][C:16]1=[O:17])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:22]([OH:40])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].[C:41](O)(=O)[CH2:42][CH2:43][CH2:44][CH2:45][C:46](O)=O.[C:51]1([CH3:61])[CH:56]=[CH:55][C:54](S(O)(=O)=O)=[CH:53][CH:52]=1>C1(C)C=CC=CC=1>[CH:1]([CH:15]([CH2:20][C:19]([O:18][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:16][CH2:15]/[CH:1]=[CH:2]\[CH2:3][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:51][CH3:61])=[O:21])[C:16]([O:40][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:17])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 196Adipic AcidHCID 6101p-Toluenesulfonic acidHCID 227803HCID 227803, compoundHCID 5284499Oleyl Alcohol

Product 1

HCID 86746458HCID 86746458, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Seventeen millimoles of tetradecenylsuccinic anhydride (5.0 gm), 34 millimoles of oleyl alcohol (9.1 gm), 50 mg of adipic acid and 10 ml of toluene were combined in a boiling flask (with attached Dean-Stark trap) and refluxed for about 6 hours in the presence of the catalyst p-toluenesulfonic acid. Excess toluene was removed at ambient pressure. The residue was applied to a silica gel column, and eluted with petroleum ether. Elution with petroleum ether gave dioleyl tetradecenylsuccinate. Oleyl alcohol and other impurities were retained on the column. The dioleyl tetradecenylsuccinate has a low melting point and can be used for the commercial production of calorie-reduced fried snack foods.

Workup

  1. customExcess toluene was removed at ambient pressure
  2. washeluted with petroleum ether
  3. washElution with petroleum ether

Sources & evidence

ORD record
ord-c6e969a2a18d4b858c7481d305f13df8
Source dataset
uspto-grants-1993_01
Patent number
US05176933

Reaction notes

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