Hydrochloric Acid → Rhein

HRID 12937Notes

Reaction equation

HRID 12937 reaction equation
CC([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:26](=[O:27])[C:14]3[CH:15]=[C:16]([C:23]([OH:25])=[O:24])[CH:17]=[C:18]([O:19]C(C)=O)[C:13]=3[C:11](=[O:12])[C:10]=12)=O.Cl>C([O-])([O-])=O.[Na+].[Na+]>[OH:19][C:18]1[C:13]2[C:11](=[O:12])[C:10]3[C:9](=[CH:8][CH:7]=[CH:6][C:5]=3[OH:4])[C:26](=[O:27])[C:14]=2[CH:15]=[C:16]([C:23]([OH:25])=[O:24])[CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 26248Diacerein

Product 1

HCID 10168Rhein

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

Diacerein (150 g, 0.41 mol) was stirred in 10% (w/w) Na2CO3 solution (4 L) resulting in a red mixture. After stirring overnight the mixture was acidified to pH2 with 5M HCl solution to give a yellow precipitate. This was filtered and dried in a vac-oven at 50° C. (168 g,>100%).

Workup

  1. customresulting in a red mixture
  2. customto give a yellow precipitate
  3. filtrationThis was filtered
  4. customdried in a vac-oven at 50° C. (168 g,>100%)

Sources & evidence

ORD record
ord-155357146c4d4f2382a0acdf7e7d0711
Source dataset
uspto-grants-2010_06
Patent number
US07728035B2

Reaction notes

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