Water → HCID 247241, compound

HRID 1158598Notes

Reaction equation

HRID 1158598 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[C:21](=[O:24])([O-])[O-:22].[K+].[K+].[OH2:27]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:22][C:21](=[O:24])[C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:2])=[O:27])=[CH:5][CH:6]=2)=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 61084-Nitrobenzoic AcidHCID 11430Potassium CarbonateHCID 123681,6-Dibromohexane

Product 1

HCID 247241HCID 247241, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

33.2 g of 4-nitrobenzoic acid (200.0 mM), 24.4 g of 1,6-dibromohexane (100.0 mM) and 41.5 g of potassium carbonate (300.0 mM) were suspended in 200 ml of DMF and this mixture was stirred at 120° C. for 2 h. It was then cooled to 60° C., poured onto 600 ml of water and the resulting suspension was stirred for 5 min. The precipitate was filtered off and the still wet cake was refluxed for 1 h in 300 ml of ethanol. It was then cooled to room temperature and filtered. The cake was washed with ethanol and dried to give 40.3 g (96.8 mM, 97%) of 6-[(4-nitrobenzoyl)oxy]hexyl 4-nitrobenzoate as a pale yellow powder.

Workup

  1. temperatureIt was then cooled to 60° C.
  2. stirringthe resulting suspension was stirred for 5 min
  3. filtrationThe precipitate was filtered off
  4. temperaturethe still wet cake was refluxed for 1 h in 300 ml of ethanol
  5. temperatureIt was then cooled to room temperature
  6. filtrationfiltered
  7. washThe cake was washed with ethanol
  8. customdried

Sources & evidence

ORD record
ord-eaa1431284df402d917faacd619c26bb
Source dataset
uspto-grants-2010_10
Patent number
US07811642B2

Reaction notes

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