5-Chlorosalicylic Acid → HCID 11044187, compound

HRID 847469Notes

Reaction equation

HRID 847469 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19](=[CH2:21])[CH3:20]>CN(C)C=O>[CH3:18][C:19](=[CH2:21])[CH2:20][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:11][CH2:7][C:6]([CH3:10])=[CH2:5]

Participants

5

Reactant 3

HCID 94475-Chlorosalicylic AcidHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate

Product 1

HCID 11044187HCID 11044187, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

When this reaction was repeated employing 2.77 Kg of 5-chloro-2-hydroxybenzoic acid, 7.6 liters of dimethylformamide, 5.55 Kg of potassium carbonate, and 3.96 liters of methallyl chloride, the cooled reaction mixture was filtered and divided into two portions. Each portion was poured separately into a mixture of 2.8 liters of hexane, 1.4 liters of ethyl acetate and 7 liters of water. The layers were separated and the aqueous layer in each case extracted again with a mixture of 1.4 liters of hexane and 0.7 liters of ethyl acetate. The organic fractions were combined and washed with 4.1 liters of water followed by a sodium chloride solution of 800 grams of sodium chloride in 4.1 liters of water. The organic extracts were combined, dried over magnesium sulfate, filtered and concentrated in vacuo to provide 4.21 Kg of the desired intermediate.

Workup

  1. customthe cooled reaction mixture
  2. filtrationwas filtered
  3. additionEach portion was poured separately into a mixture of 2.8 liters of hexane, 1.4 liters of ethyl acetate and 7 liters of water
  4. customThe layers were separated
  5. extractionthe aqueous layer in each case extracted again with a mixture of 1.4 liters of hexane and 0.7 liters of ethyl acetate
  6. washwashed with 4.1 liters of water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75b2b575b13e4f4993e78c890c129ade
Source dataset
uspto-grants-1992_08
Patent number
US05142069

Reaction notes

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