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Hydrochloric Acid → 13-Ethylgon-4-ene-3,17-dione

HRID 1077189
Notes
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Reaction equation

HRID 1077189 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20]C)[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:22])[CH3:2].CO.Cl.C(=O)(O)[O-].[Na+]>O>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:22])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 102242MethoxygonadieneHCID 516892Sodium Bicarbonate

Product 1

HCID 1037926413-Ethylgon-4-ene-3,17-dioneYield 81.3%

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Procedure

Add 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17-one (12.9 g.) with stirring under nitrogen to methanol (300 cc.) containing 11N hydrochloric acid (20 cc) and water (13 cc.). Stir two hours and add sodium bicarbonate (21 g.) portionwise. Filter the mixture and evaporate and filtrate to dryness. Recrystallize the residue from ethyl acetate (75 cc.) to obtain the title compound (10 g.), m.p. 158°-161° C; ultraviolet absorption peak at 240 mμ (ε17,800); infrared absorption peaks at 5.78, 6.00, 6.17 μ.

Workup

  1. filtrationFilter the mixture
  2. customevaporate
  3. customRecrystallize the residue from ethyl acetate (75 cc.)

Sources & evidence

ORD record
ord-8b9c644ec835475eb15ac3948aedafec
Source dataset
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03959322

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes