4-Nitrobenzoic Acid → Phenylmethyl 4-nitrobenzoate

HRID 467800

Reaction equation

HRID 467800 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].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC#N>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 84647Phenylmethyl 4-nitrobenzoateYield 89.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

15.01 g (89.9 mmol) 4-nitrobenzoic acid are suspended in 500 mL MeCN and then combined with 15.03 g (108.7 mmol, 1.2 eq) potassium carbonate. 15.4 g (90.4 mmol, 1.01 eq) benzylbromide are added dropwise with stirring and the reaction mixture is heated for 5 h with stirring at 60° C. It is combined with 750 mL distilled water, extracted 4 times with 250 mL of EE and after the organic phases have been combined dried on sodium sulphate. After all the volatile constituents have been eliminated in vacuo the crude product is suspended twice in succession in toluene and evaporated down in vacuo. 20.6 g (80.1 mmol) benzyl 4-nitrobenzoate are obtained, which is used in the next step without any further purification.

Workup

  1. temperaturethe reaction mixture is heated for 5 h
  2. stirringwith stirring at 60° C
  3. distillationdistilled water
  4. extractionextracted 4 times with 250 mL of EE
  5. customafter the organic phases have been combined dried on sodium sulphate
  6. customevaporated down in vacuo

Sources & evidence

ORD record
ord-f4c430d1f18b4c93a9736d3597c86505
Source dataset
uspto-grants-2014_01
Patent number
US08623887B2

Linked notes

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