Cyclohexanol → Cyclohexyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate

HRID 1414148Notes

Reaction equation

HRID 1414148 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:15][C:16]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:17]=1[O:18][C:19]1[CH:20]=[CH:21][C:22]([N+:28]([O-:30])=[O:29])=[C:23]([CH:27]=1)[C:24](Cl)=[O:25].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)C>[Cl:15][C:16]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:17]=1[O:18][C:19]1[CH:20]=[CH:21][C:22]([N+:28]([O-:30])=[O:29])=[C:23]([CH:27]=1)[C:24]([O:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:25]

Participants

7

Reactant 4

HCID 7966CyclohexanolHCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 130202985-(2,4-Dichlorophenoxy)-2-nitrobenzoyl chloride

Product 1

HCID 21486094Cyclohexyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of cyclohexanol (1.05g., 0.0105 mole) and triethylamine (1.10g., 0.011 mole) in toluene (30 ml.) was added 5-(2',4'-dichlorophenoxy)-2-nitrobenzoyl chloride (3.47g., 0.01 mole). A precipitate of triethylamine hydrochloride occurred immediately. The reaction solution was heated to reflux for one hour, cooled and diluted with diethyl ether (150 ml.). After filtering the triethylamine hydrochloride, the solvent was evaporated to give 4.1g. of a brown oil. A small amount of additional precipitate was filtered off. The ether was again stripped to yield 3.5g. of brown oil.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for one hour
  3. temperaturecooled
  4. filtrationAfter filtering the triethylamine hydrochloride
  5. customthe solvent was evaporated
  6. customto give 4.1g
  7. filtrationA small amount of additional precipitate was filtered off
  8. customto yield 3.5g

Sources & evidence

ORD record
ord-c9e2f7d53ff048e39212d9718131f103
Source dataset
uspto-grants-1977_01
Patent number
US04001005

Reaction notes

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