Sodium Hydroxide → HCID 19913357, compound

HRID 345276Notes

Reaction equation

HRID 345276 reaction equation
Cl(O[C:6]([C:44]1[CH:49]=[CH:48][C:47]([N:50]([CH2:53][CH3:54])[CH2:51][CH3:52])=[CH:46][CH:45]=1)([C:33]1[CH:38]=[CH:37][C:36]([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[CH:35][CH:34]=1)[CH:7]=[CH:8][CH:9]=[C:10]([C:22]1[CH:27]=[CH:26][C:25]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:24][CH:23]=1)[C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:12]=1)(=O)(=O)=O.[OH-:55].[Na+]>CO>[CH2:51]([N:50]([CH2:53][CH3:54])[C:47]1[CH:46]=[CH:45][C:44]([C:6]([C:33]2[CH:34]=[CH:35][C:36]([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[CH:37][CH:38]=2)=[CH:7][CH:8]([OH:55])[CH:9]=[C:10]([C:22]2[CH:23]=[CH:24][C:25]([N:28]([CH2:29][CH3:30])[CH2:31][CH3:32])=[CH:26][CH:27]=2)[C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:12]=2)=[CH:49][CH:48]=1)[CH3:52]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 72737836HCID 72737836, compound

Product 1

HCID 19913357HCID 19913357, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15.1 g of 1,1,5,5-tetra-(p-diethylaminophenyl)-2,4-pentadiene-1-ol perchlorate prepared in Synthesis Example 5 was dissolved in 200 ml of methanol. To this solution, 2.53 g of sodium hydroxide was added. The mixture was refluxed for 2 hours and then cooled. Crystals separated out in the reaction mixture. The crystals were filtered off, washed with water several times, and dried in reduced pressure. The crystals were recrystallized from cyclohexane, whereby 11.7 g of 1,1,5,5-tetra-(p-diethylaminophenyl)-3-hydroxy-1,4-pentadiene was obtained in the form of light green crystals. The melting point of the product was 136.5° to 137.5° C.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturecooled
  3. customCrystals separated out in the reaction mixture
  4. filtrationThe crystals were filtered off
  5. washwashed with water several times
  6. customdried in reduced pressure
  7. customThe crystals were recrystallized from cyclohexane

Sources & evidence

ORD record
ord-490ae40fa949426b9be4c1d0504adfee
Source dataset
uspto-grants-1991_10
Patent number
US05057154

Reaction notes

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