Dimethylformamide → HCID 58612418, compound

HRID 2223764Notes

Reaction equation

HRID 2223764 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:13](=[O:15])[CH3:14])[CH:8]=[C:9]([Cl:12])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].CI.[CH3:18]N(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([C:13](=[O:15])[CH3:14])[CH:8]=[C:9]([Cl:12])[C:10]=1[O:11][CH3:18])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 713465221-(3-tert-Butyl-5-chloro-4-hydroxyphenyl)ethan-1-one

Product 1

HCID 58612418HCID 58612418, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

1-(3-tert-Butyl-5-chloro-4-hydroxyphenyl)ethanone (1.65 g, 7.28 mmol) and methyl iodide (2.07 g, 14.56 mmol) were added to N,N-dimethylformamide (2.5 mL), followed by stirring on ice, and addition of potassium carbonate (1.51 g, 10.92 mmol). After 3 hours of stirring, toluene (30 mL) and water (20 mL) were added, and the solution was separated. The organic layer was washed with water (15 mL), dried, and then concentrated under reduced pressure (50° C.) to obtain 1.37 g of the subject compound as a yellowish oily substance (yield: 78.2%, HPLC purity: 99.4%)

Workup

  1. customthe solution was separated
  2. washThe organic layer was washed with water (15 mL)
  3. customdried
  4. concentrationconcentrated under reduced pressure (50° C.)

Sources & evidence

ORD record
ord-0c0eee88574f4414b5ed45f3965c6e4c
Source dataset
uspto-grants-2008_05
Patent number
US07375236B2

Reaction notes

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