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Hydrochloric Acid → 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-9-carboxylic acid

HRID 418949
Notes
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Reaction equation

HRID 418949 reaction equation
C[O:2][C:3]([CH:5]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([O:27][CH3:28])[CH:10]=2)=[O:4].CO.[OH-].[Li+].Cl>O1CCCC1>[CH3:28][O:27][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[CH:5]([C:3]([OH:4])=[O:2])[CH:18]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH:17]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 666520266-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester

Product 1

HCID 666519726-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-9-carboxylic acidYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester (1.03 g, 2.71 mmol), Methanol (20.0 mL), tetrahydrofuran (2 mL), and lithium hydroxide aqueous (5 mL), stir at reflux. After 18 hours, add 5N HCl until reaction is acidic, then extract with ethyl acetate and wash with brine. Dry the organic phase with anhydrous sodium sulfate then concentrate to yield the titled compound (0.97 g, 97%) as a white solid. TLC Rf=0.41 in 3% methanol in DCM. 1H NMR (DMSO): 12.30 (s, 1H), 7.25 (m, 3H), 6.92 (m, 3H), 6.82 (dd, 1H, J=8.6, 2.4 Hz), 4.18 (d, 1H, J=12.3 Hz), 3.76 (m, 6H), 3.42 (dd, 1H, J=12.6, 2.4 Hz), 3.27 (s, 1H), 2.50 (m, 1H), 1.89 (m, 1H), 1.59 (m, 2H), 1.40 (m, 1H), 1.23 (m, 1H), 0.99 (m, 3H); MS m/z 322 (M−44, decarbonylation).

Workup

  1. temperatureat reflux
  2. customuntil reaction
  3. extractionextract with ethyl acetate
  4. washwash with brine
  5. dry with materialDry the organic phase with anhydrous sodium sulfate
  6. concentrationthen concentrate

Sources & evidence

ORD record
ord-1655596638bc44f989958bf0deab888d
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093302B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes