Citric Acid → HCID 86733948, compound

HRID 1576262Notes

Reaction equation

HRID 1576262 reaction equation
[OH:1][C:2]1[C:7]2[CH2:8][C:9]3[C:14]([C:15]4([CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]4)[C:6]=2[CH:5]=[CH:4][CH:3]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[C:22](OC(=O)C)(=[O:24])[CH3:23].C(=O)([O-])[O-].[Na+].[Na+].[C:35]([OH:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([OH:45])=[O:44])([C:39]([OH:41])=[O:40])[OH:38]>CCOCC.O.N1C=CC=CC=1>[C:35]([OH:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([OH:45])=[O:44])([C:39]([OH:41])=[O:40])[OH:38].[C:22]([O:1][C:2]1[C:7]2[CH2:8][C:9]3[C:14]([C:15]4([CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]4)[C:6]=2[CH:5]=[CH:4][CH:3]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3)(=[O:24])[CH3:23]

Participants

8

Reactant 4

HCID 311Citric AcidHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 86733950HCID 86733950, compound

Product 1

HCID 86733948HCID 86733948, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Hydroxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine (0.9 g.) is added to pyridine (7 ml.) and acetic anhydride (5 ml.) and the solution is warmed on the steam bath for 1 hour. It is then poured into water, basified with solid sodium carbonate, and extracted with ethyl acetate. The ethyl acetate extract is washed with water, dried (MgSO4), and evaporated to give an oil to which is added an excess of a saturated solution of citric acid in ether. The resulting solid is filtered off and recrystallised three times from methanol-ether to give 4-acetoxy-1'-methyl-9,10-dihydroanthracene-9-spiro-4'-piperidine citrate m.p. 156°-159°C.

Workup

  1. temperaturethe solution is warmed on the steam bath for 1 hour
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washis washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give an oil to which
  8. filtrationThe resulting solid is filtered off
  9. customrecrystallised three times from methanol-ether

Sources & evidence

ORD record
ord-435cd71c346f4b1888ce1db2b023982e
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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