Pyridine → Cyclohexyl 4-chloro-3-nitrobenzoate

HRID 1447175Notes

Reaction equation

HRID 1447175 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 were 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. dissolutionwere 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-fb015b7b27bf4db9a07e001ca16d11b8
Source dataset
uspto-grants-1982_02
Patent number
US04316021

Reaction notes

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