4-Hydroxybenzaldehyde → HCID 19708318, compound

HRID 725670Notes

Reaction equation

HRID 725670 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([N:25]=[N:26][C:27]2[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=2)=[CH:21][CH:20]=1)([O-:18])=[O:17].O[C:37]1[CH:44]=[CH:43][C:40]([CH:41]=[O:42])=[CH:39][CH:38]=1.O>CN(C)C1C=CN=CC=1.ClCCl>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([N:25]=[N:26][C:27]2[CH:35]=[CH:34][C:30]([C:31]([O:33][C:37]3[CH:44]=[CH:43][C:40]([CH:41]=[O:42])=[CH:39][CH:38]=3)=[O:32])=[CH:29][CH:28]=2)=[CH:23][CH:24]=1)([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 197083234-[2-(4-Nitrophenyl)diazenyl]benzoic acid

Product 1

HCID 19708318HCID 19708318, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.6 g of N,N'-dicyclohexylcarbodiimide is added at room temperature while stirring to a solution of 1.0 g of 4-(4-nitrophenylazo)benzoic acid, 0.3 g of 4-hydroxybenzaldehyde and 0.04 g of 4-dimethylaminopyridine in 20 ml of dichlormethane. The reaction mixture is stirred at room temperature overnight, poured into 100 ml of water and then extracted three times with 50 ml of dichloromethane each time. The organic phases are combined, washed twice with 100 ml of water each time, dried over magnesium sulphate, filtered and the filtrate is concentrated. Chromatographic purification of the residue on silica gel with hexane/ethyl acetate (vol. 1:1) and two-fold recrystallization from ethanol of the fractions which are pure according to thin-layer chromatography gives 0.9 g of 4-[4-(4-nitrophenylazo)benzoyloxy]benzaldehyde.

Workup

  1. extractionextracted three times with 50 ml of dichloromethane each time
  2. washwashed twice with 100 ml of water each time
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated
  6. customChromatographic purification of the residue on silica gel
  7. customwith hexane/ethyl acetate (vol. 1:1) and two-fold recrystallization from ethanol of the fractions which

Sources & evidence

ORD record
ord-c7bca4095eff4a4e8a8a851bea63177d
Source dataset
uspto-grants-1998_01
Patent number
US05707544

Reaction notes

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