Carbon Disulfide → HCID 20296043, compound

HRID 1389397Notes

Reaction equation

HRID 1389397 reaction equation
[CH3:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:3]=1[O:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[C:15](OC(=O)C)(=[O:17])[CH3:16].C(=S)=S.[Cl-].[Al+3].[Cl-].[Cl-]>O>[C:15]([C:12]1[CH:11]=[C:10]([CH3:14])[C:3]([O:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])=[C:2]([CH3:1])[CH:13]=1)(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 7918Acetic AnhydrideHCID 6451240Aluminum(III) ChlorideHCID 13966814Methyl 2,6-dimethylphenoxy acetate

Product 1

HCID 20296043HCID 20296043, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7 Grams of methyl 2,6-dimethylphenoxyacetate, 3.4 ml of acetic anhydride and 100 ml of carbon disulfide were mixed at 0° C., and to the mixture was added 17.9 g of aluminum chloride, and the resulting mixture was heated until gas was evolved. After the gas-evolution was ceased, the reaction mixture was refluxed for 30 minutes under heating. Then water was added to the solution. The resulting mixture was extracted with di-isopropyl ether, washed with water, dried over anhydrous magnesium sulfate. The oily solution was concentrated to obtain an oily substance. The oily substance was chromatographed on silica gel to obtain 6.1 g of methyl 4-acetyl-2,6-dimethylphenoxyacetate, nD21.6 1.5165.

Workup

  1. temperaturethe resulting mixture was heated until gas
  2. temperaturethe reaction mixture was refluxed for 30 minutes
  3. temperatureunder heating
  4. extractionThe resulting mixture was extracted with di-isopropyl ether
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe oily solution was concentrated
  8. customto obtain an oily substance
  9. customThe oily substance was chromatographed on silica gel

Sources & evidence

ORD record
ord-4c81385b0c35495dbbcdf548189b5537
Source dataset
uspto-grants-1981_01
Patent number
US04244731

Reaction notes

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