Hydrochloric Acid → 4-[1-(4-Methoxyphenyl)ethenyl]-N,N-dimethylaniline

HRID 1763168Notes

Reaction equation

HRID 1763168 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=O)=[CH:5][CH:4]=1.O1CCC[CH2:21]1.O.Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[CH2:21])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 2825054Methanone, [4-(dimethylamino)phenyl](4-methoxyphenyl)-

Product 1

HCID 156067734-[1-(4-Methoxyphenyl)ethenyl]-N,N-dimethylaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Separately, a solution was prepared by mixing 18.2 g of 4-methoxy-4'-dimethylaminobenzophenone (melting at 126°-127° C.) and 100 ml of tetrahydrofurane, and the solution was slowly added to the liquid reaction mixture and the whole matter was stirred for one hour at a temperature of 40° to 50° C. Then the whole matter was mixed with 400 ml of water and 300 ml of toluene and after making the mixture weakly acidic by dilute hydrochloric acid, the acidified mixture was stirred for a whole at 80° C. and separated into an aqueous layer and an organic layer (toluene layer). After adding activated carbon to the toluene layer and filtering the layer while hot, toluene was distilled off from the filtrate to obtain 17.1 g of 1-(p-methoxyphenyl)-1-(p-dimethylaminophenyl)ethylene of pale yellow in color, melting at 123°-125° C.

Workup

  1. customSeparately, a solution was prepared
  2. additionthe solution was slowly added to the liquid reaction mixture
  3. stirringthe acidified mixture was stirred for a whole at 80° C.
  4. customseparated into an aqueous layer
  5. additionAfter adding activated carbon to the toluene layer
  6. filtrationfiltering the layer while hot, toluene
  7. distillationwas distilled off from the filtrate

Sources & evidence

ORD record
ord-93de7a3697854c91ac84405c2b59bb73
Source dataset
uspto-grants-1989_05
Patent number
US04835291

Reaction notes

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