Lactic Acid → beta-sitosterol Lactate

HRID 2306120Notes

Reaction equation

HRID 2306120 reaction equation
[CH3:1][CH2:2][C@@H:3]([CH:28]([CH3:30])[CH3:29])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@@:12]2([CH3:27])[CH2:13][CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@H:23]([OH:25])[CH2:24][C:19]4=[CH:18][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH3:7].[C:31]([OH:36])(=[O:35])[CH:32]([CH3:34])[OH:33].C1(C)C=CC=CC=1>O>[CH3:1][CH2:2][C@@H:3]([CH:28]([CH3:29])[CH3:30])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@@:12]2([CH3:27])[CH2:13][CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@H:23]([OH:25])[CH2:24][C:19]4=[CH:18][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH3:7].[C:31]([O-:36])(=[O:35])[CH:32]([CH3:34])[OH:33]

Participants

5

Reactant 3

HCID 612Lactic AcidHCID 1140TolueneHCID 222284(-)-beta-Sitosterol

Product 1

HCID 86758485beta-sitosterol Lactate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 g β-sitosterol, 250 g lactic acid, and 500 ml toluene were dissolved in a 5 l flask. The mixture was refluxed at 110-115° C. at the same time as water (free water+reaction water) was collected using water separation apparatus, in order to monitor the progress of the reaction. Reaction time was 11.5 h. At this point, 68 ml of water had been collected (free water: 33.8 ml+reaction water 34.2 ml), representing a 77.5% conversion in relation to the starting material. The toluene was evaporated from the reaction mixture using a rotavapor, and the product was dried in a vacuum oven at 40-60° C. The esterification experiment was repeated 5 times.

Workup

  1. customwas collected
  2. customwater separation apparatus
  3. customthe progress of the reaction
  4. customReaction time
  5. customAt this point, 68 ml of water had been collected
  6. custom(free water: 33.8 ml+reaction water 34.2 ml)
  7. customThe toluene was evaporated from the reaction mixture
  8. customthe product was dried in a vacuum oven at 40-60° C

Sources & evidence

ORD record
ord-fbea81868c184d6897ee545c557b3c4b
Source dataset
uspto-grants-2002_08
Patent number
US06441206B1

Reaction notes

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