3-Chloro-2-methyl-1-propene → Methyl 4-(acetylamino)-2-[(2-methyl-2-propenyl)oxy]benzoate

HRID 1492433Notes

Reaction equation

HRID 1492433 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([NH:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].Cl[CH2:19][C:20]([CH3:22])=[CH2:21]>CN(C)C=O>[C:13]([NH:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([O:1][CH2:21][C:20]([CH3:22])=[CH2:19])[CH:11]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 77719Methyl 4-acetamidosalicylate

Product 1

HCID 10491784Methyl 4-(acetylamino)-2-[(2-methyl-2-propenyl)oxy]benzoateYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 104.6 parts of methyl 2-hydroxy-4-(acetylamino)benzoate in 470 parts of N,N-dimethylformamide were added portionwise 24 parts of a dispersion of sodium hydride in mineral oil (50%) under a nitrogen atmosphere. After stirring for 1 hour at room temperature, there was added a solution of 55.2 parts of 3-chloro-2-methyl-1-propene in 47 parts of N,N-dimethylformamide. Stirring was continued for 3 days at 50° C. The reaction mixture was evaporated and the residue was dissolved in dichloromethane. This solution was washed with water, sodium hydroxide 10% and water and was then dried, filtered and evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 65.8 parts (50.0%) of methyl 4-(acetylamino)-2-[(2-methyl-2-propenyl)oxy]benzoate (interm. 15).

Workup

  1. stirringStirring
  2. waitwas continued for 3 days at 50° C
  3. customThe reaction mixture was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washThis solution was washed with water, sodium hydroxide 10% and water
  6. customwas then dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was crystallized from 2,2'-oxybispropane
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-6ced293f38344c5684393f19e660b68e
Source dataset
uspto-grants-1994_12
Patent number
US05374637

Reaction notes

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