Pyridine → Cyclohexyl 4-chloro-3-nitrobenzoate

HRID 1111770Notes

Reaction equation

HRID 1111770 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) for 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. temperatureThe reaction mixture was refluxed for 4 hours
  2. filtrationfiltered
  3. washThe benzene filtrate was washed successively
  4. additionwith dilute acid
  5. additiondilute base and water
  6. dry with materialThe washed benzene solution was dried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-46a2a2e18ea3487a96bdfcfb73ab8300
Source dataset
uspto-grants-1978_10
Patent number
US04118573

Reaction notes

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