Water → HCID 86676045, compound

HRID 1502187Notes

Reaction equation

HRID 1502187 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:26]4[CH:41]=[CH:40][C:29]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])=[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.[C:42]1([CH3:52])[CH:47]=[CH:46][C:45]([S:48](Cl)(=[O:50])=[O:49])=[CH:44][CH:43]=1.O>C(Cl)Cl.N1C=CC=CC=1>[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:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:39][S:48]([C:45]5[CH:46]=[CH:47][C:42]([CH3:52])=[CH:43][CH:44]=5)(=[O:50])=[O:49])=[CH:40][CH:41]=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 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 66717381HCID 66717381, compound

Product 1

HCID 86676045HCID 86676045, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

The obtained 8-[4-(3,6-diphenylcarbazol-9-yl)phenoxy]octan-1-ol (2.80 g, 5.2 mmol) was dissolved in a solvent mixture of methylene chloride (10 mL) and pyridine (5 mL). Then, p-toluenesulfonyl chloride (1.20 g, 6.3 mmol) was added to the resultant solution at −10° C., followed by stirring at room temperature. Next, the mixture was poured to water, followed by extraction with ethyl acetate. In addition, the mixture was washed with diluted hydrochloric acid and water, and dried and the solvent was evaporated, to thereby obtain a crude product. The crude product was purified through silica gel column chromatography using as an eluent a solvent mixture of ethyl acetate/toluene (1/19 by volume), to thereby obtain 1.95 g of toluene-4-sulfonic acid 8-[4-(3,6-diphenylcarbazol-9-yl)phenoxy]octyl ester as colorless plate-like crystals.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washIn addition, the mixture was washed with diluted hydrochloric acid and water
  3. customdried
  4. customthe solvent was evaporated
  5. customto thereby obtain a crude product
  6. customThe crude product was purified through silica gel column chromatography
  7. additiona solvent mixture of ethyl acetate/toluene (1/19 by volume)

Sources & evidence

ORD record
ord-36a4531bb1c242ca9d629e4227e99226
Source dataset
uspto-grants-2015_12
Patent number
US09206202B2

Reaction notes

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