Water → HCID 66717381, compound

HRID 1502186Notes

Reaction equation

HRID 1502186 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:26]4[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=4)[C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][OH:44].O>CN(C)C=O>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:26]4[CH:27]=[CH:28][C:29]([O:32][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][OH:44])=[CH:30][CH:31]=4)[C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=4)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1626071-Octanol, 8-bromo-HCID 66717009HCID 66717009, compound

Product 1

HCID 66717381HCID 66717381, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The obtained 3,6-diphenyl-9-(4-hydroxyphenyl)carbazole (1.54 g, 3.7 mmol) was dissolved in N,N-dimethylformamide (20 mL). Under cooling with ice water, 55% by mass sodium hydride (0.25 g, 5.7 mmol) was added to the resultant solution, followed by stirring for 1 hour. Next, 8-bromo-1-octanol (1.16 g, 5.5 mmol) was added thereto, and the resultant mixture was stirred for 3 hours at room temperature. In addition, the mixture was poured to water, followed by extraction with ethyl acetate. Next, the mixture was washed with water and dried and the solvent was evaporated, to thereby obtain 1.90 g of 8-[4-(3,6-diphenylcarbazol-9-yl)phenoxy]octan-1-ol.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washNext, the mixture was washed with water
  3. customdried
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4e76edfb3db641ea9d4fc467f9089c40
Source dataset
uspto-grants-2015_12
Patent number
US09206202B2

Reaction notes

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