Potassium Carbonate → Methyl 3-(2-(tert-butoxy)-2-oxoethoxy)benzoate

HRID 1524261Notes

Reaction equation

HRID 1524261 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Br[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([O:1][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 16094634Methyl 3-(2-(tert-butoxy)-2-oxoethoxy)benzoateYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 3-hydroxybenzoate (1.00 g, 6.57 mmol) in N,N-dimethylformamide (60 mL) add tert-butyl bromoacetate (1.10 mL, 7.44 mmol) followed by potassium carbonate (4.0 g, 29 mmol) of. Heat the mixture at 70° C. for 5 hours, Cool to room temperature and pour over ice. Allow the mixture to sit until all of the ice melts during which time a solid precipitates from solution. Collect the white solid by filtration, wash with water and dry on the filter pad to provide 1.49 g of 3-tert-butoxycarbonylmethoxy-benzoic acid methyl ester.

Workup

  1. temperatureCool to room temperature
  2. additionpour over ice
  3. customprecipitates from solution
  4. customCollect the white solid
  5. filtrationby filtration
  6. washwash with water
  7. customdry on the filter pad

Sources & evidence

ORD record
ord-54a24cb810604203ae9023deb5883883
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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