Water → 2-(2,4-Bis(tert-pentyl)phenoxy)-N-(3,5-dichloro-4-ethyl-2-hydroxyphenyl)butyramide

HRID 1635695Notes

Reaction equation

HRID 1635695 reaction equation
O.C([O-])(=O)C.[Na+].[Cl:7][C:8]1[C:9]([OH:18])=[C:10]([CH:12]=[C:13]([Cl:17])[C:14]=1[CH2:15][CH3:16])[NH2:11].[CH3:19][C:20]([C:24]1[CH:36]=[C:35]([C:37]([CH3:41])([CH3:40])[CH2:38][CH3:39])[CH:34]=[CH:33][C:25]=1[O:26][CH:27]([CH2:31][CH3:32])[C:28](Cl)=[O:29])([CH3:23])[CH2:21][CH3:22]>CCCCCCC.C1(C)C=CC=CC=1>[CH3:23][C:20]([C:24]1[CH:36]=[C:35]([C:37]([CH3:40])([CH3:41])[CH2:38][CH3:39])[CH:34]=[CH:33][C:25]=1[O:26][CH:27]([CH2:31][CH3:32])[C:28]([NH:11][C:10]1[CH:12]=[C:13]([Cl:17])[C:14]([CH2:15][CH3:16])=[C:8]([Cl:7])[C:9]=1[OH:18])=[O:29])([CH3:19])[CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 1703932-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chlorideHCID 517045Sodium AcetateHCID 117696522,4-Dichloro-3-ethyl-6-aminophenol

Product 1

HCID 1755692-(2,4-Bis(tert-pentyl)phenoxy)-N-(3,5-dichloro-4-ethyl-2-hydroxyphenyl)butyramideYield 90%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8900HeptaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a 4-neck flask with a gas inlet, condenser, thermometer, and addition funnel, 50 mL of deionized water and 31 g of sodium acetate was added and stirring was continued until the solid dissolved. At this point, 57 g of heptane, 20 g of toluene, and 30 g (0.146 moles) of 3,5-dichloro-4-ethyl-2-hydroxyaniline was added and the 2-phase mixture was warmed to 60° C. A solution of 53.2 g of 2-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyryl chloride (0.157 moles, 8% excess) in 53 g of heptane was then added at 60° C.-65° C. The reaction was held for 2 hr at 60° C. -65° C., upon which time the area percent product by HPLC was 92% on a solvent-free basis. The two-phase mixture was heated to 75° C.-80° C. and held for 15 minutes. The agitator was stopped and the lower layer was decanted. The product solution was washed twice with 42 g of deionized water, cooled to 70° C. and seeded. The product slurry was cooled to 0° C.-5° C., and the product was collected by filtration, washed with cold heptane, and dried to give 66.9 g (90% yield), with an assay of 99.5% (wt.).

Workup

  1. additionTo a 4-neck flask with a gas inlet, condenser, thermometer, and addition funnel
  2. dissolutiondissolved
  3. temperatureThe two-phase mixture was heated to 75° C.-80° C.
  4. waitheld for 15 minutes
  5. customthe lower layer was decanted
  6. washThe product solution was washed twice with 42 g of deionized water
  7. temperaturecooled to 70° C.
  8. temperatureThe product slurry was cooled to 0° C.-5° C.
  9. filtrationthe product was collected by filtration
  10. washwashed with cold heptane
  11. customdried
  12. customto give 66.9 g (90% yield)

Sources & evidence

ORD record
ord-88940dfb4fac4624821d9320e6d7f190
Source dataset
uspto-grants-2003_01
Patent number
US06509500B2

Reaction notes

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