N,N-Dimethylaniline → N-[4-hydroxy-3-[2-methyl-1-(4-methylphenyl)-1-propenyl]-2,5,6-trimethylphenyl]formamide

HRID 29120Notes

Reaction equation

HRID 29120 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9]CC(C)=CC2C=CC(C)=CC=2)[CH:5]=[C:4]([CH3:21])[C:3]=1[NH:22][CH:23]=[O:24].[C:25](=O)([O-])[O-].[K+].[K+].CN(C)[C:33]1[CH:38]=CC=C[CH:34]=1.[CH3:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>>[OH:9][C:6]1[C:5]([CH3:25])=[C:4]([CH3:21])[C:3]([NH:22][CH:23]=[O:24])=[C:2]([CH3:1])[C:7]=1[C:8]([C:42]1[CH:41]=[CH:40][C:45]([CH3:46])=[CH:44][CH:43]=1)=[C:33]([CH3:38])[CH3:34]

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 8900Heptane2×HCID 11430Potassium CarbonateHCID 73856749N-[2,3,6-Trimethyl-4-[[2-methyl-3-(4-methylphenyl)-2-propenyl]oxy]phenyl]formamide

Product 1

HCID 22501141N-[4-hydroxy-3-[2-methyl-1-(4-methylphenyl)-1-propenyl]-2,5,6-trimethylphenyl]formamideYield 86.9%

Conditions

Temperature
190 °C

Procedure

A mixture of N-[2,3,6-trimethyl-4-[[2-methyl-3-(4-methylphenyl)-2-propenyl]oxy]phenyl]formamide (920 g), potassium carbonate (4.6 g) and N,N-dimethylaniline (2760 ml) was stirred at 190° C. for 4 hr under nitrogen stream. The mixture was cooled to 100° C. and heptane (1840 ml) was added dropwise thereto. The mixture was further cooled to 30° C. and heptane (3680 ml) was added dropwise thereto. The mixture was stirred at the same temperature for 1 hr, and the precipitated crystals were collected by filtration and washed with heptane to give the title compound (799.5 g, yield 86.9%).

Workup

  1. temperatureThe mixture was cooled to 100° C.
  2. temperatureThe mixture was further cooled to 30° C.
  3. stirringThe mixture was stirred at the same temperature for 1 hr
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with heptane

Sources & evidence

ORD record
ord-929d3e8a42634e4ba14bfbfc337f01a7
Source dataset
uspto-grants-2008_09
Patent number
US07420070B2

Reaction notes

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