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

HRID 1843689Notes

Reaction equation

HRID 1843689 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[OH:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:17][O:16][C:14]([C:13]1[CH:12]=[C:11]([CH:20]=[CH:19][CH:18]=1)[O:10][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[O:15]

Participants

5

Reactant 3

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

Product 1

HCID 16094634Methyl 3-(2-(tert-butoxy)-2-oxoethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of t-butyl bromoacetate (506 g, 2.59 mol), methyl 3-hydroxybenzoate (395 g, 2.60 mol) and potassium carbonate (789 g, 5.71 mol) in DMF (2 L) was stirred at room temperature for two hours. The reaction mixture was concentrated and then water (1 L) was added, followed by extraction with ethyl acetate (2 L). The organic layer was washed with water (1 L) twice, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain t-butyl [3-(methoxycarbonyl)phenoxy]acetate as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater (1 L) was added
  3. extractionfollowed by extraction with ethyl acetate (2 L)
  4. washThe organic layer was washed with water (1 L) twice
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-195eee29a295416385005b9cd3af36c2
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

Loading…