Citric Acid → HCID 86733942, compound

HRID 1576260Notes

Reaction equation

HRID 1576260 reaction equation
[OH:1][CH:2]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]2([CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.O.O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O.[OH-].[Na+].[C:42]([OH:54])(=[O:53])[CH2:43][C:44]([CH2:49][C:50]([OH:52])=[O:51])([C:46]([OH:48])=[O:47])[OH:45]>CC(C)=O.C(Cl)(Cl)Cl.O>[C:42]([OH:54])(=[O:53])[CH2:43][C:44]([CH2:49][C:50]([OH:52])=[O:51])([C:46]([OH:48])=[O:47])[OH:45].[CH3:15][N:12]1[CH2:13][CH2:14][C:9]2([C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:2](=[O:1])[C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:10][CH2:11]1

Participants

9

Reactant 5

HCID 311Citric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 108005Sodium dichromate dihydrateHCID 86733944HCID 86733944, compound

Product 1

HCID 86733942HCID 86733942, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent3×HCID 6212ChloroformSolvent

Procedure

To 10-hydroxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine (whose preparation is described in Example 2) (11.5 g.) in acetone (1250 ml.) is added, dropwise with stirring, a solution of oxidising agent (32 ml.), made from sodium dichromate dihydrate (10 g.), water (30 ml.) and concentrated sulphuric acid (7.4 ml.), made up to 50 ml. with water. After addition is complete, the reaction mixture is stirred for 1 hour and is then poured into water (3 l.) basified with 2N sodium hydroxide, and extracted three times with ether. The ether extracts are combined, washed with water and with brine and evaporated to give a brown oil which is dissolved in the minimum volume of chloroform and treated with an excess of saturated ethereal citric acid. The resulting precipitate is crystallised from methanol-ether to give 1'-methyl-10-oxo-9,10-dihydroanthracene-9-spiro-4'-piperidine citrate m.p. 172°-173°C.

Workup

  1. additionAfter addition
  2. stirringthe reaction mixture is stirred for 1 hour
  3. extractionextracted three times with ether
  4. washwashed with water and with brine
  5. customevaporated
  6. customto give a brown oil which
  7. customThe resulting precipitate is crystallised from methanol-ether

Sources & evidence

ORD record
ord-30e6af74806740e393be704cf7851429
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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