N,N-Dimethylaniline → HCID 14838650, compound

HRID 1681861Notes

Reaction equation

HRID 1681861 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])C=C.CN(C)[C:18]1[CH:23]=CC=C[CH:19]=1>>[Cl:15][C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([OH:4])[C:14]=1[CH2:23][CH:18]=[CH2:19]

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 14838649HCID 14838649, compound

Product 1

HCID 14838650HCID 14838650, compoundYield 71.1%

Procedure

A solution of methyl 2-allyloxy-4-chlorobenzoate (3f) (50.6 g, 0.22 mol) in 100 ml of N,N-dimethylaniline was heated under argon in an oil bath at 190°-205° C. for 20 hours. The solvent was removed by distillation and the residue purified by column chromatography (silica gel, CH2Cl2 /hexane) to give 4f (36.0 g, 71.1% yield) as a very light oil. IR (nujol) 1665 (C=O) cm-1. NMR (CDCl3) δ11.23 (s, 1H, OH), 7.47 (d, 1H, J=9 Hz, aromatic proton meta to Cl), 6.77 (d, 1H, aromatic proton alpha to Cl), 6.17-4.77 (m, 3H, olefinic protons), 3.87 (s, 3H, CH3) and 3.50 (m, 2H, CH2).

Workup

  1. customThe solvent was removed by distillation
  2. customthe residue purified by column chromatography (silica gel, CH2Cl2 /hexane)

Sources & evidence

ORD record
ord-93ebdafc35b346caa1156a1fc5c66936
Source dataset
uspto-grants-1992_12
Patent number
US05175173

Reaction notes

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