Hydrochloric Acid → Isogarcinol

HRID 716504Notes

Reaction equation

HRID 716504 reaction equation
[CH3:1][C:2]([CH3:44])=[CH:3][CH2:4][C@H:5]1[C:15]([CH3:17])([CH3:16])[C@:12]2([CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[C:13](=[O:14])[C@@:7]([CH2:34][C@@H:35]([C:41]([CH3:43])=[CH2:42])[CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])([C:8]([OH:33])=[C:9]([C:23]([C:25]3[CH:26]=[CH:27][C:28]([OH:32])=[C:29]([OH:31])[CH:30]=3)=[O:24])[C:10]2=[O:11])[CH2:6]1.Cl>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:44])=[CH:3][CH2:4][C@H:5]1[C:15]([CH3:16])([CH3:17])[C@:12]2([CH2:18][CH:19]=[C:20]([CH3:21])[CH3:22])[C:13](=[O:14])[C@@:7]3([C:8](=[C:9]([C:23]([C:25]4[CH:26]=[CH:27][C:28]([OH:32])=[C:29]([OH:31])[CH:30]=4)=[O:24])[C:10]2=[O:11])[O:33][C:41]([CH3:43])([CH3:42])[C@@H:35]([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[CH2:34]3)[CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178448266HCID 178448266, compound

Product 1

HCID 11135781IsogarcinolYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

150 mg (0.249 mmol) of garcinol in toluene (1.2 mL) was stirred with 60 μL of concentrated hydrochloric acid at room temperature for 10 hours. The resulting mixture was allowed to stand in a refrigerator overnight, and the precipitated solid was collected by filtration and rinsed with 6 mL of water. 0.6 mL of acetonitrile was added to the solid to form a slurry, and the slurry was filtered. The slurry obtained from the filtrate was filtered. The collected solids were combined and dried to give 68.7 mg of isogarcinol (yield 46%).

Workup

  1. customto stand in a refrigerator overnight
  2. filtrationthe precipitated solid was collected by filtration
  3. washrinsed with 6 mL of water
  4. addition0.6 mL of acetonitrile was added to the solid
  5. customto form a slurry
  6. filtrationthe slurry was filtered
  7. customThe slurry obtained from the filtrate
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-8b4edd11c3f14cb2b8cb1354cbfe38a7
Source dataset
uspto-grants-2015_11
Patent number
US09187728B2

Reaction notes

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