Hydrochloric Acid → alpha-(4-Chlorophenyl)-2-methoxy-4-nitrobenzeneacetonitrile

HRID 1165839Notes

Reaction equation

HRID 1165839 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[OH-].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]#[N:24])=[CH:18][CH:17]=1.Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O1CCCC1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[O:11][CH3:12])[C:23]#[N:24])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 705192-Chloro-5-nitroanisoleHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 23035215alpha-(4-Chlorophenyl)-2-methoxy-4-nitrobenzeneacetonitrile

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 68 parts of 1-chloro-2-methoxy-4-nitrobenzene, 230 parts of a sodium hydroxide solution 50%, 5 parts of N,N,N-triethylbenzenemethanaminium chloride and 360 parts of tetrahydrofuran is added dropwise, during a 5 minutes period, a solution of 43.2 parts of 4-chlorobenzeneacetonitrile in 90 parts of tetrahydrofuran. Upon completion, stirring is continued for 4 hours at 60° C. The reaction mixture is poured into 2000 parts of crushed ice. The whole is acidified with concentrated hydrochloric acid. The layers are separated. The aqueous phase is extracted with dichloromethane. The combined extracts are dried, filtered and evaporated. The residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding at α-(4-chlorophenyl)-2-methoxy-4-nitrobenzeneacetonitrile.

Workup

  1. additionis added dropwise, during a 5 minutes period
  2. additionThe reaction mixture is poured into 2000 parts of crushed ice
  3. customThe layers are separated
  4. extractionThe aqueous phase is extracted with dichloromethane
  5. customThe combined extracts are dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 2,2'-oxybispropane
  9. filtrationThe product is filtered off
  10. customdried

Sources & evidence

ORD record
ord-1325d139c5a84b63a55fe1eb14766557
Source dataset
uspto-grants-1990_03
Patent number
US04912106

Reaction notes

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