Pyridine → Cyclohexyl 4-chloro-3-nitrobenzoate

HRID 2048963Notes

Reaction equation

HRID 2048963 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[Cl:13])[C:7](Cl)=[O:8])([O-:3])=[O:2].N1C=CC=CC=1.[CH:20]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[Cl:13])[C:7]([O:26][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7966CyclohexanolHCID 1234774-Chloro-3-nitrobenzoyl chloride

Product 1

HCID 12837987Cyclohexyl 4-chloro-3-nitrobenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Twelve grams (0.055 mole) fo crude 3-nitro-4-chlorobenzoyl chloride was dissolved in 200 ml. of benzene. Eight milliliters of pyridine were added to the reaction mixture. Six milliliters of cyclohexanol were dissolved in 50 ml. of benzene and the solution was added dropwise to the acid chloride-pyridine mixture. The reaction mixture was refluxed for 4 hours and filtered. The benzene filtrate was washed successively with dilute acid, dilute base and water. The washed benzene solution was dried and evaporated in vacuo to yield 12.5 g (88 percent) of cyclohexyl 3-nitro-4-chlorobenzoate, mp 57°-58° C.

Workup

  1. dissolutionwas dissolved in 200 ml
  2. temperatureThe reaction mixture was refluxed for 4 hours
  3. filtrationfiltered
  4. washThe benzene filtrate was washed successively
  5. additionwith dilute acid
  6. additiondilute base and water
  7. dry with materialThe washed benzene solution was dried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-3d503c149e4d4f1783e2bf068d6248b1
Source dataset
uspto-grants-1980_04
Patent number
US04196125

Reaction notes

Loading…