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Water → HCID 18979554, compound

HRID 2392587
Notes
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Reaction equation

HRID 2392587 reaction equation
C([N:3]([CH2:6][CH3:7])CC)C.CS(Cl)(=O)=O.[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([OH:41])=[O:40])=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)(=[O:16])[CH:14]=[CH2:15].O[C:43]1[CH:44]=[C:45]([CH:48]=[CH:49][C:50]=1[OH:51])[C:46]#N.[OH2:52]>O1CCCC1.CN(C)C1C=CN=CC=1>[C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([O:41][C:28]3[CH:29]=[C:7]([CH:31]=[CH:32][C:27]=3[O:52][C:39]([C:36]3[CH:37]=[CH:38][C:46]([C:45]4[CH:48]=[CH:49][C:50]([O:51][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:13](=[O:16])[CH:14]=[CH2:15])=[CH:43][CH:44]=4)=[CH:34][CH:35]=3)=[O:40])[C:6]#[N:3])=[O:40])=[CH:35][CH:34]=2)=[CH:31][CH:32]=1)(=[O:16])[CH:14]=[CH2:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 870653,4-DihydroxybenzonitrileHCID 18979499HCID 18979499, compound

Product 1

HCID 18979554HCID 18979554, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

0.9 g of triethylamine and then 0.5 g of methanesulphonyl chloride were added dropwise at -25° C. while stirring to a solution of 2.0 g of 4-(8-acryloyloxyoctyloxy)biphenyl-4'-carboxylic acid in 40 ml of tetrahydrofuran. The reaction mixture was stirred at -25° C. for 1 hour, then treated with 0.25 g of 3,4-dihydroxybenzonitrile and 0.05 g of 4-(dimethylamino)pyridine, stirred at room temperature overnight, poured into 100 ml of water and then extracted three times with 50 ml of diethyl ether each time. The organic phases were combined, washed twice with 100 ml of water each time, dried over magnesium sulphate, filtered and the filtrate was concentrated. Chromatographic purification of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which were pure according to thin-layer chromatography gave 1.0 g of 3,4-bis[4-(8-acryloyloxyoctyloxy)biphenyl-4'-carbonyloxy]benzonitrile.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionextracted three times with 50 ml of diethyl ether each time
  3. washwashed twice with 100 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customChromatographic purification of the residue on silica gel
  8. customwith cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which

Sources & evidence

ORD record
ord-bcec63a8d5c540ef94a9d2d0399c143b
Source dataset
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05800733

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes