Sodium Hydroxide → HCID 19384484, compound

HRID 2399810Notes

Reaction equation

HRID 2399810 reaction equation
[OH-:1].[Na+].[CH2:3]([CH:11]1[C:16]2=[C:17]3[CH2:23][CH2:22][CH2:21][CH2:20][C:18]3=[N:19][C:15]2=[C:14]([CH2:24][C:25]2[O:29][C:28]([CH:30]=[O:31])=[CH:27][CH:26]=2)[CH:13]=[CH:12]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>O.[N+]([O-])([O-])=O.[Ag+]>[CH2:3]([CH:11]1[C:16]2=[C:17]3[CH2:23][CH2:22][CH2:21][CH2:20][C:18]3=[N:19][C:15]2=[C:14]([CH2:24][C:25]2[O:29][C:28]([C:30]([OH:1])=[O:31])=[CH:27][CH:26]=2)[CH:13]=[CH:12]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86748996HCID 86748996, compound

Product 1

HCID 19384484HCID 19384484, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

To freshly prepared silver oxide obtained by treating 1.9 g of silver nitrate with 0.9 g of sodium hydroxide in 8 mL of water was added at 0°-5° C. a solution of 1.4 g of aldehyde from Example 159. After 2 hours of stirring at room temperature the reaction mixture was filtered on celite. The filtrate was acidified with 2N-HCl and the product extracted with ethyl acetate. Repeated crystallizations of the crude material (1.3 g) from ethyl acetate-hexane gave 0.8 g (54.7%) of 5-[(1,2,3,4-tetra-hydro-9-octyl-9H-dibenzo[b,d]pyrrol-6-yl)-methyl]-2-furancarboxylic acid as a pale yellow solid, mp 152.5°-155.0° C.

Workup

  1. filtrationwas filtered on celite
  2. extractionthe product extracted with ethyl acetate
  3. customcrystallizations of the crude material (1.3 g) from ethyl acetate-hexane

Sources & evidence

ORD record
ord-44bbaff188d348ba9627974de05730a9
Source dataset
uspto-grants-1995_09
Patent number
US05451600

Reaction notes

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