Acetophenone → 25287-19-8

HRID 1088513Notes

Reaction equation

HRID 1088513 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>O>[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([N:15]=[C:1]([CH3:2])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 78124-Chloroaniline

Product 1

HCID 73699925287-19-8

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of acetophenone (132 ml), p-chloroaniline (128 g) benzene (150 ml) was refluxed in the presence of molecular sieve (40 g) with continuous removal of water. The crude product was crystallized from ethanol to give p-chloro-N-(α-methyl benzylidene) aniline (XVII). It was then hydrogenated using 5% Pd/C as the catalyst and 95% ethanol as the solvent. The crude product was crystallized from ethanol and pet. ether to give p-chloro-N-(α-methyl benzyl) aniline (XVIII). XVIII had a melting point of 62° C.

Workup

  1. customThe crude product was crystallized from ethanol

Sources & evidence

ORD record
ord-2402d525c2624a5bba98f5d1a1e29193
Source dataset
uspto-grants-1990_10
Patent number
US04962234

Reaction notes

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