Thionyl Chloride → (2,6-Dimethylphenoxy)acetyl Chloride

HRID 1457362Notes

Reaction equation

HRID 1457362 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[O:4][CH2:5][C:6](O)=[O:7].S(Cl)([Cl:16])=O>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[O:4][CH2:5][C:6]([Cl:16])=[O:7]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 101369(2,6-Dimethylphenoxy)acetic acid

Product 1

HCID 12353505(2,6-Dimethylphenoxy)acetyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

2,6-dimethylphenoxyacetylchloride is prepared in a separate vessel as follows: 2,6-dimethylphenoxyacetic acid, 5.4060 grams (29.99 mmol) is charged to a 50 mL round bottom flask equipped with a teflon-coated magnetic stir bar. Toluene, 15 mL is added stirring is initiated and thionyl chloride, 9.0 mL (123.3 mmol) is added followed by one drop of N,N-dimethylformamide at ambient temperature. After seven hours, the reaction mixture is heated to 65° C. for thirty minutes and allowed to cool to ambient temperature. The solution is concentrated at 60° C. and ca. 60 mm Hg pressure to remove all volatiles. The residue is diluted with toluene, 25 mL and reconcentrated. This is repeated a second time to give a final residue.

Workup

  1. customequipped with a teflon-coated magnetic stir bar
  2. temperatureto cool to ambient temperature
  3. concentrationThe solution is concentrated at 60° C.
  4. customca. 60 mm Hg pressure to remove all volatiles
  5. additionThe residue is diluted with toluene, 25 mL

Sources & evidence

ORD record
ord-b96ed95fa80f4915a63751c673dc98b9
Source dataset
uspto-grants-1998_12
Patent number
US05847169

Reaction notes

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