Hydrochloric Acid → HCID 86733952, compound

HRID 1576267Notes

Reaction equation

HRID 1576267 reaction equation
C[Li].[OH:3][C:4]1[C:9]2[C:10](=[O:24])[C:11]3[C:16]([C:17]4([CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]4)[C:8]=2[CH:7]=[CH:6][CH:5]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3.Cl.[C:26](=O)([O-])[O-].[Na+].[Na+]>CCOCC.O>[OH:3][C:4]1[C:9]2[C:10]([OH:24])([CH3:26])[C:11]3[C:16]([C:17]4([CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]4)[C:8]=2[CH:7]=[CH:6][CH:5]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 86733953HCID 86733953, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 86733952HCID 86733952, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Methyl lithium in ether (5 ml., 1.5M) is added dropwise with stirring under nitrogen to 4-hydroxy-1'-methyl-10-oxo-9,10-dihydroanthracene-9-spiro-4'-piperidine (0.7 g.) in dry ether (25 ml.) and the mixture is stirred for 1 hour then diluted with water, acidified (2N hydrochloric acid), basified with sodium carbonate, and extracted with ethyl acetate. The ethyl acetate extract is washed with water and with brine, dried (MgSO4), evaporated, and the residue is recrystallised from ethanol to give 4,10-dihydroxy-1',10-dimethyl-9,10-dihydroanthracene-9-spiro-4'-piperidine, m.p. 151°-154°C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washis washed with water and with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customthe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-1e761840240a4730a344cbcada5faf98
Source dataset
uspto-grants-1976_09
Patent number
US03979513

Reaction notes

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