2-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chloride → 2-(2,4-Bis(tert-pentyl)phenoxy)-N-(3,5-dichloro-4-ethyl-2-hydroxyphenyl)butyramide

HRID 1635697

Reaction equation

HRID 1635697 reaction equation
C(=O)(O)[O-].[K+].[Cl:6][C:7]1[C:8]([OH:17])=[C:9]([CH:11]=[C:12]([Cl:16])[C:13]=1[CH2:14][CH3:15])[NH2:10].[CH3:18][C:19]([C:23]1[CH:35]=[C:34]([C:36]([CH3:40])([CH3:39])[CH2:37][CH3:38])[CH:33]=[CH:32][C:24]=1[O:25][CH:26]([CH2:30][CH3:31])[C:27](Cl)=[O:28])([CH3:22])[CH2:20][CH3:21]>C(O)(C)C.O.C1(C)C=CC=CC=1.CCCCCCC>[CH3:22][C:19]([C:23]1[CH:35]=[C:34]([C:36]([CH3:39])([CH3:40])[CH2:37][CH3:38])[CH:33]=[CH:32][C:24]=1[O:25][CH:26]([CH2:30][CH3:31])[C:27]([NH:10][C:9]1[CH:11]=[C:12]([Cl:16])[C:13]([CH2:14][CH3:15])=[C:7]([Cl:6])[C:8]=1[OH:17])=[O:28])([CH3:18])[CH2:20][CH3:21]

Participants

8

Reactant 3

HCID 1703932-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chlorideHCID 516893Potassium BicarbonateHCID 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)butyramide

Reagents, catalysts & solvents 4

HCID 962WaterSolvent3×HCID 1140TolueneSolvent2×HCID 3776IsopropanolSolvent2×HCID 8900HeptaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A heel was created via batch mode by first adding of 16 g (0.16 moles) of potassium bicarbonate, and 55 g of deionized water, and stirring until all of the solid had dissolved. Then 24 g of isopropanol, 30 g (0.146 moles) of 3,5-dichloro-4-ethyl-2-hydroxyaniline (the amine), 120 g of heptane, and 20 g of toluene were then added. The contents of the reactor system were heated to approximately 60° C. while agitating at 400 rpm. To this 2-phase mixture 57.5 g (0.169 moles) of 2-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyryl chloride (the acid chloride) were added over approximately 45 minutes. The analysis of the upper phase of the mixture was 91.8% on a solvent-free basis. The reaction temperature was raised to reflux. (68° C.-75° C.), and the continuous feeds were started at the following rates to provide six hours of residence time: 0.67 g/min of water; 0.51 g/min (1.36 mmoles/min) of a 55.5% (wt.) solution of the amine in isopropanol; and 1.82 g/min (1.48 mmoles/min)of a solution of the acid chloride solution 27.5% (wt.) in a mixture of 6 parts of heptane and 1 part of toluene. The water phase became highly acidic since the pH was not controlled in this run.

Workup

  1. dissolutionhad dissolved
  2. stirringwhile agitating at 400 rpm
  3. temperatureThe reaction temperature was raised
  4. temperatureto reflux
  5. custom(68° C.-75° C.)
  6. customto provide six hours of residence time

Sources & evidence

ORD record
ord-1be0f21de6e443deb867c8555dbd9093
Source dataset
uspto-grants-2003_01
Patent number
US06509500B2

Linked notes

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