Toluene → HCID 101361972, compound

HRID 1754021Notes

Reaction equation

HRID 1754021 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:21]([OH:28])[C@@H:22]([C@@H:24]([CH2:26][OH:27])O)[OH:23].[C:29]1([CH3:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:36]1([CH3:46])[CH:41]=[CH:40][C:39](S(O)(=O)=O)=[CH:38][CH:37]=1>O>[C:1]([O:20][C@H:24]([C@@H:22]([CH2:21][OH:28])[O:23][C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:37][CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:36]\[CH2:46][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:29][CH3:35])[CH2:26][OH:27])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 222285ErythritolHCID 445639Oleic Acid

Product 1

HCID 101361972HCID 101361972, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

347 g (1.23 mol) oleic acid and 50 g (0.41 mol) erythritol were added into a 2 L three-neck flask which was equipped with a stirrer, a condenser and an addition funnel. To the flask was added 1 L toluene as a water carrier, followed by addition of a reaction catalyst p-toluenesulfonic acid (7.9 g, 2 wt %). The mixture was refluxed at 135±2° C. for 26 hours. When the reaction was ended, the reaction system was allowed to cool to room temperature and stand for 2 hours. The solid was removed by filtration, and the liquid phase was washed with a saturated sodium bicarbonate aqueous solution and petroleum ether in sequence. 160 g solid product was obtained after drying by rotary evaporation. A solution of the product in (CD3)2CO was tested by 1H NMR (400 MHz), and the results are as follows: (400 MHz): δ 0.89 (3H, t, J=6.8 Hz), 1.30 (20H, m), 1.60 (4H, m), 2.05 (8H, m), 2.34 (4H, t, J=7.6 Hz), 3.72 (2H, dd, J=4 Hz), 4.02 (2H, dd, J=5.6 Hz), 5.36 (6H, m). The above results show that the product obtained was a product formed by esterification of the hydroxyl groups on the 2,3-positions of erythritol, i.e. erythritol dioleate. The purity was determined by HPLC to be 91%.

Workup

  1. customwas equipped with a stirrer, a condenser and an addition funnel
  2. temperatureto cool to room temperature
  3. customThe solid was removed by filtration
  4. washthe liquid phase was washed with a saturated sodium bicarbonate aqueous solution and petroleum ether in sequence

Sources & evidence

ORD record
ord-6cf88e8aa566459cb0ed2a22f830ca5a
Source dataset
uspto-grants-2015_10
Patent number
US09169191B2

Reaction notes

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