Sulfuric Acid → 604-33-1

HRID 1752828Notes

Reaction equation

HRID 1752828 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]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:21][CH:22]([CH2:24][CH2:25][CH2:26][C@H:27]([C@@H:29]1[C@:47]2([CH3:48])[C@H:32]([C@H:33]3[C@H:44]([CH2:45][CH2:46]2)[C@:42]2([CH3:43])[C:36]([CH2:37][C@H:38]([CH2:40][CH2:41]2)O)=[CH:35][CH2:34]3)[CH2:31][CH2:30]1)[CH3:28])[CH3:23].OS(O)(=O)=O>C(Cl)Cl>[CH3:18][CH2:17][CH2:16][CH2:15][CH2:14]/[CH:13]=[CH:12]\[CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:20][C@@H:38]1[CH2:37][C:36]2[C@@:42]([CH3:43])([C@@H:44]3[C@@H:33]([CH2:34][CH:35]=2)[C@@H:32]2[CH2:31][CH2:30][C@H:29]([C@@H:27]([CH2:26][CH2:25][CH2:24][CH:22]([CH3:21])[CH3:23])[CH3:28])[C@@:47]2([CH3:48])[CH2:46][CH2:45]3)[CH2:41][CH2:40]1)=[O:19]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 5997CholesterolHCID 5280450Linoleic Acid

Product 1

HCID 5287939604-33-1

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DCPLA (1 g), cholesterol (1 g), CH2Cl2 (20 ml), and concentrated H2SO4 (1 μl) were combined and refluxed overnight. The product was washed with sodium phosphate (pH 7.0, 5 ml) and purified by flash chromatography to yield the DCPLA-cholesteryl ester. Linoleic acid (1 g), cholesterol (1 g), CH2Cl2 (20 ml), and concentrated H2SO4 (20 μl) were combined and refluxed overnight. The product was washed with sodium phosphate (pH 7.0, 5 ml) and purified by flash chromatography to yield the cholesteryl linoleate.

Workup

  1. temperaturerefluxed overnight
  2. washThe product was washed with sodium phosphate (pH 7.0, 5 ml)
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-daa834afa72047a8ade89b94b43295e2
Source dataset
uspto-grants-2015_10
Patent number
US09163032B2

Reaction notes

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