Sodium hydride → Methyl 3-tert-butyl-5-(2-methoxyethoxy)benzoate

HRID 532403Notes

Reaction equation

HRID 532403 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([OH:15])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][CH2:18][O:19][CH3:20].[H-].[Na+]>CN(C=O)C.CC(=O)OCC>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:15][CH2:17][CH2:18][O:19][CH3:20])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 53399216Methyl 3-tert-butyl-5-hydroxybenzoate

Product 1

HCID 58136955Methyl 3-tert-butyl-5-(2-methoxyethoxy)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-tert-butyl-5-hydroxybenzoate (O6.043; 2.18 g) and 1-bromo-2-methoxyethane (1.18 ml) were dissolved in DMF (30 ml) and sodium hydride (301 mg) was added while stirring. After stirring at RT for 2 h, the solvent was drawn off. The residue was taken up in EA, and the mixture was washed with water, dried and concentrated. The residue was purified using silica gel (80 g cartridge, n-heptane/MtB ether gradient of 0-30% in 60 min). 2.0 g of the title compound were obtained.

Workup

  1. stirringAfter stirring at RT for 2 h
  2. washthe mixture was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified
  6. customsilica gel (80 g cartridge, n-heptane/MtB ether gradient of 0-30% in 60 min)

Sources & evidence

ORD record
ord-eb5498070b264b238739844a7256c6d4
Source dataset
uspto-grants-2014_10
Patent number
US08853206B2

Reaction notes

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