Sodium Hydroxide → HCID 86733961, compound

HRID 1576270Notes

Reaction equation

HRID 1576270 reaction equation
C(O)(=O)/C=C\C(O)=[O:5].[CH2:9]([N:12]1[CH2:17][CH2:16][C:15]2([C:30]3[CH:29]=[CH:28][CH:27]=[C:26]([O:31][CH3:32])[C:25]=3[CH2:24][C:23]3[C:18]2=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][CH2:13]1)[CH:10]=[CH2:11].[OH-].[Na+]>C(O)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[CH2:9]([N:12]1[CH2:13][CH2:14][C:15]2([C:30]3[CH:29]=[CH:28][CH:27]=[C:26]([O:31][CH3:32])[C:25]=3[C:24](=[O:5])[C:23]3[C:18]2=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:16][CH2:17]1)[CH:10]=[CH2:11]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86733962HCID 86733962, compound

Product 1

HCID 86733961HCID 86733961, compound

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

1'-Allyl-4-methoxy-9,10-dihydroanthracene-9-spiro-4'-piperidine maleate (7.2 g.) in glacial acetic acid (20 ml.) is treated dropwise with stirring with chromium trioxide [60 ml. of a solution of CrO3 (21 g.) in glacial acetic acid (190 ml.) and water (10 ml.)]. The reaction mixture is stirred for 3 hours, diluted with water, basified (NaOH), and extracted with ether. The ether extract is washed with water and with brine, dried (MgSO4) and evaporated to give a solid which is recrystallised from cyclohexane to give 1'-allyl-4-methoxy-10-oxo-9,10-dihydroanthracene-9-spiro-4'-piperidine, m.p. 115-117°C.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washis washed with water and with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a solid which
  7. customis recrystallised from cyclohexane

Sources & evidence

ORD record
ord-cf478dc2fd2a419aa0c0ec08044d6bdf
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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