Dichloromethane → Benzoic acid, 4-nitro-, 2-ethylhexyl ester

HRID 600159

Reaction equation

HRID 600159 reaction equation
[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])[CH3:2].ClCCl.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14]>N1C=CC=CC=1>[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][O:5][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 77202-EthylhexanolHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 591313Benzoic acid, 4-nitro-, 2-ethylhexyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the 250 ml 3-necked flask was added 10.0 gm 2-ethyl 1-hexanol, 100 ml dichloromethane, and 6.0 gm pyridine and the contents were stirred for 10 minutes. To this mixture, 14.2 gm 4-nitro benzoyl chloride was added slowly and stirred under reflux conditions for 2 hrs. The reaction mixture was then cooled, washed with 20% aqueous ammonium hydroxide. The organic layer was washed with 1N hydrochloric acid and brine, and dried over anhydrous sodium sulfate to give a crude product (˜65% yield).

Workup

  1. stirringstirred under reflux conditions for 2 hrs
  2. temperatureThe reaction mixture was then cooled
  3. washwashed with 20% aqueous ammonium hydroxide
  4. washThe organic layer was washed with 1N hydrochloric acid and brine
  5. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-93155600f00349d3b8e04ec8a340f00e
Source dataset
uspto-grants-2011_03
Patent number
US07901839B2

Linked notes

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