Hydrochloric Acid → HCID 19384513, compound

HRID 2399791Notes

Reaction equation

HRID 2399791 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[CH:14][CH:15]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:16]3[C:20]=2[N:19]=[C:18]2[CH2:21][CH2:22][CH2:23][CH2:24][C:17]=32)=[CH:8][CH:9]=1)=[O:4].[OH-].[K+].Cl>CO.O>[CH2:25]([CH:15]1[C:16]2=[C:17]3[CH2:24][CH2:23][CH2:22][CH2:21][C:18]3=[N:19][C:20]2=[C:12](/[CH:11]=[CH:10]/[C:7]2[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=2)[CH:13]=[CH:14]1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 67784333HCID 67784333, compound

Product 1

HCID 19384513HCID 19384513, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 6.5 g of (E)-5-[2-(1,2,3,4-tetrahydro-9-octyl-9H-dibenzo [b,d]pyrrol-6-yl)ethenyl]-2-furancarboxylic acid methyl ester from Example 33 in 72 ml of methanol was treated with a solution of 4.9 g of 87% potassium hydroxide in 18 ml of water. The mixture was refluxed for 45 minutes, cooled, diluted with water, acidified with 2N HCl and then extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 6.0 g of crude acid. Crystallization from ethyl acetate and hexane afforded 4.0 g (63.7%) of (E)-5-[2-(1,2,3,4-tetrahydro-9-octyl-9H-dibenzo[b,d]pyrrol-6-yl)ethenyl]-2-furancarboxylic acid as yellow crystals, mp 142°-144° C.

Workup

  1. temperatureThe mixture was refluxed for 45 minutes
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give 6.0 g of crude acid
  8. customCrystallization from ethyl acetate and hexane

Sources & evidence

ORD record
ord-2a84c9002b0542faad35b32ec32bc887
Source dataset
uspto-grants-1995_09
Patent number
US05451600

Reaction notes

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