Dimethylformamide → HCID 20043642, compound

HRID 1761929Notes

Reaction equation

HRID 1761929 reaction equation
[CH:1]([C:3]1[C:4]([OH:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:2].Cl[CH2:15][C:16]([O:18]C(C)(C)C)=[O:17].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][CH:12]=[C:3]([CH:1]=[O:2])[C:4]=1[O:13][CH2:15][C:16]([OH:18])=[O:17])=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetateHCID 345559Methyl 3-formyl-2-hydroxybenzoate

Product 1

HCID 20043642HCID 20043642, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.0 g of methyl 3-formyl-2-hydroxybenzoate, 3.31 g of t-butyl chloroacetate, 12.0 g of potassium carbonate and 40 ml of dimethylformamide is heated at 70° C. for 2.5 hours. After cooling, the reaction mixture is poured into water and the aqueous mixture is extracted with ethyl acetate. The extract is washed with an aqueous saturated sodium chloride solution, dried and evaporated to remove solvent. The residue is dissolved in trifluoroacetic acid and the solution is stirred at room temperature for 30 minutes. The reaction mixture is concentrated under reduced pressure and the residue is treated with ether to give 2.09 g of (2-methoxycarbonyl-6-formylphenoxy)acetic acid as pale yellow powder.

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous mixture is extracted with ethyl acetate
  3. washThe extract is washed with an aqueous saturated sodium chloride solution
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. dissolutionThe residue is dissolved in trifluoroacetic acid
  8. concentrationThe reaction mixture is concentrated under reduced pressure
  9. additionthe residue is treated with ether

Sources & evidence

ORD record
ord-baf6f164c562429993615a573d946bf1
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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