Methanol → HCID 86734451, compound

HRID 1415583Notes

Reaction equation

HRID 1415583 reaction equation
[OH-].[K+].CO.[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH2:13][C:14]#[N:15].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([N+:24]([O-])=[O:25])[CH:18]=1>O.C(O)(=O)C>[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[C:13](=[C:22]1[CH:21]=[C:20]([CH3:23])[C:19](=[N:24][OH:25])[CH:18]=[C:17]1[Cl:16])[C:14]#[N:15]

Participants

7

Reactant 4

HCID 887Methanol2×HCID 6975Benzene, 4-chloro-1-methyl-2-nitro-HCID 14797Potassium HydroxideHCID 805662,4-Dichlorophenylacetonitrile

Product 1

HCID 86734451HCID 86734451, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 75 parts of potassium hydroxide in 240 parts of methanol, are added 27 parts of 2,4-dichlorobenzeneacetonitrile. Then there is added a solution of 25.5 parts of 1-chloro-4-methyl-3-nitrobenzene in 40 parts of methanol (exothermic reaction: temperature rises to 40° C). Stirring is continued for 2 hours while meantime the mixture is allowed to cool to 20° -25° C. 1000 parts of water are added. Upon the addition of a mixture of acetic acid and water (1:1 by volume), an oil is precipitated. The supernatant aqueous phase is decanted and the oil is taken up in methylbenzene. The solution is evaporated. The oily residue is triturated in a mixture of 2,2'-oxybispropane and petroleumether, yielding 2,4-dichloro-α-[2-chloro-4-(hydroxyimino)-5-methyl-2,5-cyclohexadien-1-ylidene]benzeneacetonitrile.

Workup

  1. temperatureto cool to 20° -25° C
  2. customan oil is precipitated
  3. customThe supernatant aqueous phase is decanted
  4. customThe solution is evaporated
  5. customThe oily residue is triturated in a mixture of 2,2'-oxybispropane and petroleumether

Sources & evidence

ORD record
ord-98faf7a368b54d83be5e5eac21b7f669
Source dataset
uspto-grants-1977_01
Patent number
US04005218

Reaction notes

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