2-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chloride → HCID 20313399, compound

HRID 2419504Notes

Reaction equation

HRID 2419504 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:4]=1[NH:5][C:6](=[O:16])[CH2:7][C:8](=[O:15])[C:9]([S:12][CH2:13][CH3:14])([CH3:11])[CH3:10].C([O-])(=O)C.[Na+].[C:29]([C:34]1[CH:46]=[C:45]([C:47]([CH2:50][CH3:51])([CH3:49])[CH3:48])[CH:44]=[CH:43][C:35]=1[O:36][CH:37]([CH2:41][CH3:42])[C:38](Cl)=[O:39])([CH2:32][CH3:33])([CH3:31])[CH3:30]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]([NH:21][C:38](=[O:39])[CH:37]([O:36][C:35]2[CH:43]=[CH:44][C:45]([C:47]([CH2:50][CH3:51])([CH3:49])[CH3:48])=[CH:46][C:34]=2[C:29]([CH2:32][CH3:33])([CH3:31])[CH3:30])[CH2:41][CH3:42])=[CH:17][C:4]=1[NH:5][C:6](=[O:16])[CH2:7][C:8](=[O:15])[C:9]([S:12][CH2:13][CH3:14])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 1703932-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chlorideHCID 517045Sodium AcetateHCID 20313363HCID 20313363, compound

Product 1

HCID 20313399HCID 20313399, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 82 g of 2'-methoxy-5'-nitro-(2-ethylthio-2methylpropionyl)acetanilide obtained in Synthesis Example 3 and 800 ml of glacial acetic acid was heated to 90° C. To the mixture, 80 g of reduced iron was gradually added over a four minute period under a nitrogen atmosphere and with stirring. The reaction mixture was cooled to room temperature, and 24.1 g of sodium acetate and then 97 g of 2-(2,4-di-tert-amylphenoxy)butyryl chloride were added, and the mixture was stirred vigorously for 1 hour. The reaction mixture was filtered to remove the insoluble substances. The filtrate was poured into 1 liter of ethyl acetate, washed 4 times, each with 1 liter of a saturated aqueous sodium chloride solution, and then dried with sodium sulfate. After distilling off ethyl acetate, the residue was recrystallized from ethanol to obtain 110 g (yield 75%) of Coupler (13) having a melting point of 65° to 67° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred vigorously for 1 hour
  3. filtrationThe reaction mixture was filtered
  4. customto remove the insoluble substances
  5. additionThe filtrate was poured into 1 liter of ethyl acetate
  6. washwashed 4 times
  7. dry with materialeach with 1 liter of a saturated aqueous sodium chloride solution, and then dried with sodium sulfate
  8. distillationAfter distilling off ethyl acetate
  9. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-5807b498d225425ca9bbad10e0c01f81
Source dataset
uspto-grants-1978_08
Patent number
US04106942

Reaction notes

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